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{{Huge|Sphingolipid (スフィンゴ脂質)}}
{{Huge|{{Bilingual|スフィンゴ脂質|Sphingolipid}}}}
{{LB/Header}}
{{Hierarchy|{{PAGENAME}}}}
{{Hierarchy|{{PAGENAME}}}}
{| style="float:left"
| __TOC__
|}
=={{Bilingual|概要|Class Overview}}==


==Class Overview==
{{Twocolumn|
Three Sphingolipid categories (LBS) exist in this database.
|このデータベースではスフィンゴ脂質を以下に分けています。
}}


<center>
<center>
{| class="wikitable" border="1" cellpadding="2" cellspacing="1" margin: 1em 1em 1em 1em"
{|  
|+ Table 1. Classification of Sphingolipid [[Image:LBS.png|120px]]  
|-
|- valign="top"
| style="vertical-align:top" width="33%"|
|align="center"|Sphingoid base<br/>and ceramide<br/>[[Volatile:ListMol|LBS*****--|LBS*****--: ]]<br/>？
[[:Category:LBSB| '''Ceramide''']]<br/>{{LBS/Cer|OH}}<br/><small>セラミド</small>
|align="center"|Glycolipid<br/>(incl. ceramide)<br/> [[Volatile:ListMol|LBS*****##|LBS*****##:]]<br/>?
| style="vertical-align:top" width="33%"|
|align="center"|Phospholipid<br/>(incl. ceramide)<br/> [[Volatile:ListMol|LBS*****PP|LBS*****PP:]]<br/>?
'''Glycosphingolipid'''<br/>{{LBS/Cer|O-(sugar)}}<br/><small>スフィンゴ糖脂質</small>
| style="vertical-align:top" width="33%"|
[[:Category:LBSP| '''Phosphosphingolipid''']]<br/>{{LBS/Cer|O-(phosphate)}}<br/><small>スフィンゴリン脂質</small>
|-
|
*[[:Category:LBSB|Long-chain base and ceramide]]
|
*[[:Category:LBSC|Cerebroside <small>(monohexosyl ceramides)</small>]]
*[[:Category:LBSG|Acidic glycosphingolipid]]
|
*[[:Category:LBSP|Sphingomyelin, CPE, CAEP and GIPC]]
|}
|}
</center>
</center>


==Design of Sphingoid identifiers <small>ID番号の設計</small>==
<center>
<center>
12-DIGIT
{| class="wikitable"
|<big>
[[:Category:LBS/Search|{{Bilingual|スフィンゴ脂質検索画面にいく|Go to Sphingolipid search.}}]]
</big>
|}
</center>
 
 
=={{Bilingual|スフィンゴ脂質|Sphingolipid}}==
 
==={{Bilingual|表記法|Notation}}===
{| class="wikitable collapsible collapsed" style="width:80%"
!colspan="4" align="center" style="background:lightgray"| Symbol Abbreviations (e.g. Glc = glucose)
|-
!colspan="4" align="center" style="background:lightgray"| Backbones
{{#repeatnum:LBS/AbbrevRow|1|
Cer && ceramide && セラミド &&
Sph && sphingosine && スフィンゴシン &&
}}
|-
!colspan="4" align="center" style="background:lightgray"| Sugars
{{#repeatnum:LBS/AbbrevRow|1|
Glc && glucose && グルコース && C6H12O6 &&
Gal && galactose && ガラクトース && C6H12O6 &&
GlcNAc && ''N''-acetyl-glucosamine && ''N''-アセチルグルコサミン && C8H15NO6
GalNAc && ''N''-acetyl-galactosamine && ''N''-アセチルガラクトサミン && C8H15NO6
GlcN && glucosamine && グルコサミン && C6H13NO5
GalN && galactosamine && ガラクトサミン && C6H13NO5
GlcA && glucuronic acid && グルクロン酸 && C6H10O7
GalA && galacturonic acid && ガラクツロン酸 && C6H10O7 &&
Man && mannose && マンノース && C6H12O6 && 18950
Rha && rhamnose (= 6-deoxy-mannose) && ラムノース (6-デオキシマンノース) && C6H12O5 && 19233
Ins && inositol && イノシトール && C6H12O6 && 892
Fuc && fucose (= 6-deoxy-galactose) && フコース (6-デオキシガラクトース) && C6H12O5 && 17106
Ara && arabinose && アラビノース && C5H10O5 && 5460291
Xyl && xylose && キシロース && C5H10O5 && 135191
NeuNH && (deacetyl) neuraminic acid<br/>(pyruvate + mannosamine) && ノイラミン酸<br/>(ピルビン酸＋マンノサミン) && C9H17N1O8 && 513472
NeuAc && ''N''-acetyl-neuraminic acid && ''N''-アセチルノイラミン酸 && C11H19NO9 && 439197
NeuGc && ''N''-glycolyl-neuraminic acid && ''N''-グリコリルノイラミン酸 && C11H19NO10 && 123802
Kdn && 2-keto-3-deoxy-D-glycero-<br/>D-galacto-nononic acid && デアミノノイラミン酸 && C9H16O9 && 13991616
}}
|-
!colspan="4" align="center" style="background:lightgray"| Modifiers
{{#repeatnum:LBS/AbbrevRow|1|
AEPn && aminoethylphosphonic acid, or<br/>(2-aminoethyl)hydroxyphosphoryl- && アミノエチルホスホン酸（C-P結合）
MAEPn && ''N''-methyl aminoethylphosphonic acid, or<br/>(''N''-methyl-2-aminoethyl) hydroxyphosphoryl- && AEPnの''N''-メチル体（C-P結合）
EtnP && phosphoethanolamine (PEA), or<br/>2-aminoethanolphospho- && ホスホエタノールアミン
PC && Phosphocholine && ホスホコリン
Butenyl && Butenyl && ブテニル基
Me && Methyl && メチル基
Et && Ethyl && エチル基
}}
|}
 
==={{Bilingual|分類体系|Page/ID-Code Design}}===
{{Twocolumn|
Major series of phosphosphingolipids are determined by molecules bound to their phosphates, and the series of glycosphingolipids are determined by oligosaccharides bound to their ceramides. The IUPAC series of glycosphingolipids (1977) were based on the order and bonding patterns of four sugars rooting at the long-chain base. Our series, however, are based on three sugars. Two original series, Echino and Schisto, are also added.
|スフィンゴリン脂質はリン酸に結合する分子や糖の種類、スフィンゴ糖脂質はセラミドに結合する糖鎖により系列を作成しています。1977年にIUPACが提唱したスフィンゴ糖脂質の系列は、長鎖塩基に結合する四糖の並びと結合を基準にしています。ここではより広い糖鎖の系列を検索できるよう、三糖を基準に分類しています。また新たにEchinoとSchistoの系列を加えています。
}}
 
{|
|
<table border=1>
<table border=1>
<tr>
<tr>
<td style="background-color:yellowgreen;" width=15px align="center"><big>L</big>
<td style="background-color:yellowgreen;" width=20px align="center"><big>L</big>
<td style="background-color:yellowgreen;" width=15px align="center"><big>B</big>
<td style="background-color:yellowgreen;" width=20px align="center"><big>B</big>
<td style="background-color:darkseagreen;" width=15px align="center"><big>S</big>
<td style="background-color:yellowgreen;" width=20px align="center"><big>S</big>
<td style="background-color:tomato;" width=15px align="center"><big>''x''</big>
<td style="background-color:green;" width=20px align="center"><big>''G/P''</big>
<td style="background-color:tomato;" width=15px align="center"><big>''x''</big>
<td style="background-color:Blue; color:white" width=20px align="center"><big>''s1''</big>
<td style="background-color:purple;" width=15px align="center"><big>''y''</big>
<td style="background-color:Blue; color:white" width=20px align="center"><big>''s2''</big>
<td style="background-color:firebrick;" width=15px align="center"><big>''z''</big>
<td style="background-color:tomato; color:white" width=20px align="center"><big>''n1''</big>
<td style="background-color:firebrick;" width=15px align="center"><big>''z''</big>
<td style="background-color:tomato; color:white" width=20px align="center"><big>''n2''</big>
<td style="background-color:green;" width=15px align="center"><big>''w''</big>
<td style="background-color:firebrick; color:white" width=20px align="center"><big>''y''</big>
<td style="background-color:green;" width=15px align="center"><big>''w''</big>
<td style="background-color:white;" width=20px align="center"><big>''c1''</big>
<td style="background-color:white;" width=15px align="center"><big>''c''</big>
<td style="background-color:white;" width=20px align="center"><big>''c2''</big>
<td style="background-color:white;" width=15px align="center"><big>''c''</big>
</tr>
</tr>
</table>
</table>
</center>
| &nbsp;
|
{| class="wikitable"
! '''G/P''' || '''G''' (glyco) || '''P''' (phospho)
|-
! '''s1, s2'''
|colspan="3"| structure code as explained below
|-
! '''n1, n2'''
|colspan="2"| number of sugars (2 digits)
|-
! '''y'''
|colspan="2"| number of sialic acids (1 digit)
|-
! '''c1, c2'''
|colspan="2"| serial numbers
|}
|}
 
==={{Bilingual|スフィンゴ糖脂質１文字目|First (s1) Digit for Glycosphingolipid}}===
<span id="SphingolipidClass"></span>
{| class="wikitable" style="text-align:right; background-color:white"
! First sugar || Code || Root sequence
! colspan=2 | Major Series
|-
! Cerebroside
| colspan="3" style="text-align:left" | '''For GalCer and GlcCer, visit [[:Category:LBSC|this page]].'''
|-
! starting with<br/><big>Galactose</big>
| {{#volatile:ListMol/LBStitle|<b>G1</b>|LBSG1}} <br /> ({{#volatile:ClassMatrix|{{#countTitle:LBSG1}} items|LBSG1.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids}})
|style="text-align:right"| '''Gal'''-Cer
|
{| style="width:100%;"
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|Gala / Neogala|Mainchain.*Gala1-4?6?Galb1-Cer}}
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|Gala1-4/6Galb1-Cer}}
|-
|style="border:0;text-align:left"|{{#volatile:ListMol/LBS|Spirometo|Mainchain.*Galb1-4Glcb1-3Galb1-Cer}}
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|Galb1-4Glcb1-3Galb1-Cer}}
|}
|-
! rowspan="8" | starting with<br/><big>Glucose</big>
|-
| {{#volatile:ListMol/LBStitle|<b>G2</b>|LBSG2}} <br /> ({{#volatile:ClassMatrix|{{#countTitle:LBSG2}} items|LBSG2.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids}})
|style="text-align:right"| '''GalNAc<sub>&beta;</sub>'''-Gal<sub>&beta;</sub>-Glc<sub>&beta;</sub>-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|Ganglio|Mainchain.*GalNAcb1-4Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|GalNAcb1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|Isoganglio|Mainchain.*GalNAcb1-3Galb1-4Glcb1-Cer}}<ref name="iso">In IUPAC, "iso" refers to a change from position 4 to position 3.</ref>
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|GalNAcb1-3Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|Lactoganglio|Structure.*GlcNAcb1-3\(.*GalNAcb1-4\)Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|GlcNAcb1-3(GalNAcb1-4)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|a-series|Structure.*\(?NeuAca2-3\)?Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|GalNAcb1-4(NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|b-series|Structure.*\(?NeuAca2-8NeuAca2-3\)?Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|GalNAcb1-4(NeuAca2-8NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|c-series|Structure.*\(?NeuAca2-8NeuAca2-8NeuAca2-3\)?Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|GalNAcb1-4(NeuAca2-8NeuAca2-8NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|&alpha;-series|Structure.*\(?NeuAca2-6\)?GalNAcb1-4Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|...(NeuAca2-6)GalNAcb1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|&beta;-series|Structure.*\(?NeuAca2-8NeuAca2-6\)?GalNAcb1-4Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|...(NeuAca2-8NeuAca2-6)GalNAcb1-4Galb1-4Glcb1-Cer}}
|}
|-
| {{#volatile:ListMol/LBStitle|<b>G3</b>|LBSG3}} <br /> ({{#volatile:ClassMatrix|{{#countTitle:LBSG3}} items|LBSG3.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids}})
|style="text-align:right"| '''GlcNAc<sub>&beta;</sub>'''-Gal<sub>&beta;</sub>-Glc<sub>&beta;</sub>-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|Lacto|Mainchain.*Galb1-3GlcNAcb1-3Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|Galb1-3GlcNAcb1-3Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|Neolacto|Mainchain.*Gal.1-4GlcNAcb1-3Galb1-4Glcb1-Cer}}<ref name="neo">In IUPAC, "neo" refers to a change from position 3 to position 4.</ref>
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|Galb1-4GlcNAcb1-3Galb1-4Glcb1-Cer}}
|}
|-
| {{#volatile:ListMol/LBStitle|<b>G4</b>|LBSG4}} <br /> ({{#volatile:ClassMatrix|{{#countTitle:LBSG4}} items|LBSG4.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids}})
|style="text-align:right"| '''Gal<sub>&alpha;</sub>'''-Gal<sub>&beta;</sub>-Glc<sub>&beta;</sub>-Cer
|
{| style="width:100%"
|-
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|Globo|Mainchain.*Gala1-4Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|Gala1-4Galb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|Isoglobo|Mainchain.*Gala1-3Galb1-4Glcb1-Cer}}<ref name="iso"/>
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|Gala1-3Galb1-4Glcb1-Cer}}
|}
|-
| {{#volatile:ListMol/LBStitle|<b>G5</b>|LBSG5}} <br /> ({{#volatile:ClassMatrix|{{#countTitle:LBSG5}} items|LBSG5.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids}})
|style="text-align:right"| Gal-Glc-Cer<br/>(Other than G2&sim;G4)
|
{| style="width:100%"
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|Muco|Mainchain.*Galb1-4Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|Galb1-4Galb1-4Glcb1-Cer}}
|}
|-
| {{#volatile:ListMol/LBStitle|<b>G6</b>|LBSG6}} <br /> ({{#volatile:ClassMatrix|{{#countTitle:LBSG6}} items|LBSG6.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids}})
|style="text-align:right"| '''Man'''-Glc<sub>&beta;</sub>-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|Arthro|Mainchain.*GlcNAcb1-3Manb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|GlcNAcb1-3Manb1-4Glcb1-Cer}}
|-
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|Mollu|Mainchain.*Mana1-3Manb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|Mana1-3Manb1-4Glcb1-Cer}}
|}
|-
| {{#volatile:ListMol/LBStitle|<b>G7</b>|LBSG7}} <br /> ({{#volatile:ClassMatrix|{{#countTitle:LBSG7}} items|LBSG7.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids}})
|style="text-align:right"| '''NeuAc'''/'''NeuGc'''-Glc<sub>&beta;</sub>-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|Echino|Mainchain.*Neu(A~G)c.2-6Glcb1-Cer}}
|style="border:0;text-align:right"| <font color=purple>'''NeuGc'''</font> or {{#invoke:LBS|FormatSugar|NeuAca2-6Glcb1-Cer}}
|}
|-
| {{#volatile:ListMol/LBStitle|<b>G8</b>|LBSG8}} <br /> ({{#volatile:ClassMatrix|{{#countTitle:LBSG8}} items|LBSG8.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids}})
|style="text-align:right"| '''GalNAc'''-Glc-Cer
|
{| style="width:100%"
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|Schisto|Mainchain.*GalNAc.1-4Glc.1-Cer}}<ref>Makaaru CK, Damian RT, Smith DF, Cummings RD. "The human blood fluke Schistosoma mansoni synthesizes a novel type of glycosphingolipid" J Biol Chem 1992 267:2251-2257 PMID 1733932</ref>
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|GalNAcb1-4Glcb1-Cer}}
|}
|-
! starting with<br/><big>Other Sugars</big>
| {{#volatile:ListMol/LBStitle|<b>G</b>(<b>A</b>&sim;<b>R</b>)|LBSG(A~B~C~D~E~F~G~H~J~K~M~N~O~P~Q~R)}}
|colspan="2"| Symbols follow the Sugar-digit table.
|}
<references/>
 
==={{Bilingual|スフィンゴリン脂質１文字目|First (s1) Digit for Phosphosphingolipid}}===
{| class="wikitable" style="text-align:right; background-color:white"
! First sugar || Code || Root sequence
!colspan="2"| Major Series
|-
! No Sugar Attached
| '''P1''' ([[:Category:LBSP|LBSP]])
| R-P-Cer
| Sphingomyelin and Ceramide phosphoetanolamine<br/>(Visit [[:Category:LBSP|this page]].)
|-
! rowspan="4" | starting with<br/><big>Inositol</big>
| {{#volatile:ListMol/LBStitle|<b>P2</b>|LBSP2}} <br /> ({{#countTitle:LBSP2}} items)
| style="text-align:right"| '''GlcN'''<sub>&alpha;/&beta;1&minus;2/6</sub>Ins<sub>1</sub>-P-Cer
|
{|style="width:100%"
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|Protozoa & Fungi-specific|Mainchain.*GlcN.1-.Ins-P-Cer}}
| style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|GlcNa/b1-2/6Ins1-P-Cer}}
|}
|-
| {{#volatile:ListMol/LBStitle|<b>P3</b>|LBSP3}} <br /> ({{#countTitle:LBSP3}} items)
|style="text-align:right"| '''GlcA'''<sub>&alpha;/&beta;1&minus;2/6</sub>Ins<sub>1</sub>-P-Cer
|
{|style="width:100%"
|style="border:0;text-align:left"| {{#volatile:ListMol/LBS|Plant-specific|Mainchain.*GlcA.1-.Ins-P-Cer}}
|style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|GlcAa/b1-2/6Ins1-P-Cer}}
|}
|-
| {{#volatile:ListMol/LBStitle|<b>P4</b>|LBSP4}} <br /> ({{#countTitle:LBSP4}} items)
| style="text-align:right"| '''Man'''<sub>&alpha;/&beta;1&minus;2/6</sub>Ins<sub>1</sub>-P-Cer
|
{| style="width:100%"
| style="border:0;text-align:left"| {{#volatile:ListMol/LBS|Fungi-specific|Mainchain.*Man.1-.Ins-P-Cer}}
| style="border:0;text-align:right"| {{#invoke:LBS|FormatSugar|Mana/b1-2/6Ins1-P-Cer}}
|}
|-
| {{#volatile:ListMol/LBStitle|<b>P5</b>|LBSP5}} <br /> ({{#countTitle:LBSP5}} items)
| style="text-align:right"| Gal, Glc, and Others
| style="text-align:right"| {{#invoke:LBS|FormatSugar|X-Ins1-P-Cer}}
|}
 
==={{Bilingual|コード２文字目|Second (s2) Digit}}===
<span id="SphingolipidSugar"></span>
{{Bilingual|クリックすると一覧が出ます。記号の略称については|Click to see the full list. For abbreviations, see}} [[#Notation]].
 
{|
|-
| valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''A'''
| Glc [[File:LBS-Monomer-Glc.png]]
|-
! '''B'''
| Gal [[File:LBS-Monomer-Gal.png]]
|-
! '''C'''
| GlcNAc [[File:LBS-Monomer-GlcNAc.png]]
|-
! '''D'''
| GalNAc [[File:LBS-Monomer-GalNAc.png]]
|-
! '''E'''
| GlcN [[File:LBS-Monomer-GlcN.png]]
|-
! '''F'''
| GalN [[File:LBS-Monomer-GalN.png]]
|-
! '''G'''
| GlcA [[File:LBS-Monomer-GlcA.png]]
|-
! '''H'''
| GalA [[File:LBS-Monomer-GalA.png]]
|-
! '''I'''
| not used
|}
|valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''J'''
| {{#volatile:ListMol/LBS|Mannose|Structure.*Man}} [[File:LBS-Monomer-Man.png]]
|-
! '''K'''
| {{#volatile:ListMol/LBS|Rhamnose|Structure.*Rha}} [[File:LBS-Monomer-Rha.png]]
|-
! '''L'''
| {{#volatile:ListMol/LBS|Inositol|Structure.*Ins(Me)?-P-[^Cer]}}
|-
! '''M'''
| Fucose ({{#volatile:ListMol/LBS| 1|Structure[^F]+Fuc[^F]+$}}, {{#volatile:ListMol/LBS|2|Structure([^F]+Fuc){2}[^F]+$}}, {{#volatile:ListMol/LBS|>3|Structure([^F]+Fuc){3} }}) [[File:LBS-Monomer-Fuc.png]]
|-
! '''N'''
| {{#volatile:ListMol/LBS|Arabinose|Structure.*Ara}} [[File:LBS-Monomer-Ara.png]]
|-
! '''O'''
| {{#volatile:ListMol/LBS|Xylose|Structure.*Xyl}} [[File:LBS-Monomer-Xyl.png]]
|-
! '''P'''
| {{#volatile:ListMol/LBS|NeuAc / NeuNH|Structure.*(NeuAc~NeuNH)}} [[File:LBS-Monomer-NeuAc.png]]
|-
! '''Q'''
| {{#volatile:ListMol/LBS|NeuGc|Structure.*(NeuGc)}} [[File:LBS-Monomer-NeuGc.png]]
|-
! '''R'''
| {{#volatile:ListMol/LBS|Kdn|Structure.*(KDN)}} [[File:LBS-Monomer-KDN.png]]
|}
|valign="top"|
{| class="wikitable"
|-
! Code || Structure
|-
! '''S'''
| {{#volatile:ListMol/LBS|Phosphate (except GIPC)|Structure.*(Phospho)}} [[File:LBS-Monomer-P.png]]
|-
! '''T'''
| {{#volatile:ListMol/LBS|(M)AEPn|Structure.*(AEPn)}}, {{#volatile:ListMol/LBS|EtnP|Structure.*(EtnP)}}, {{#volatile:ListMol/LBS|PC|Structure.*(PC)}} [[File:LBS-Monomer-AEPn.png]]
|-
! '''U'''
| {{#volatile:ListMol/LBS|Sulfate|Structure.*Sulfo}} [[File:LBS-Monomer-S.png]]
|-
! '''V'''
| acyl/alkyl/alkenyl chain [[File:LBS-Monomer-Alkyl.png]]
|}
 
=={{Bilingual|生合成|Biosynthesis}}==
{{Twocolumn|
Sphingosine is synthesized from decarboxylating condensation of palmitoyl CoA with serine on the ER membrane.  It is a 18-carbon amino alcohol (16 carbons from palmitic acid and 2 from serine) with one unsaturated bond (trans-form) at the C-4 position (2-amino-4-octadecene-1,3-diol). ([[:Category:LBS/Biosynthesis|more details]])
|
スフィンゴシンはパルミトイルCoAがアミノ酸セリンと脱炭酸縮合して生成します。炭素を18個含むアミノアルコール(16個がパルミチン酸、2個がセリン由来)でトランス型の不飽和結合をC-4に1つ含みます。（[[:Category:LBS/Biosynthesis|詳細はこちら]]）
}}
 
 
=={{Bilingual|スフィンゴ脂質の歴史|History of Sphingolipids}}==
{{Twocolumn|
{{Twocolumn|
* ''x'' ... carbon chain length
Sphingolipids were first isolated from brain by J.L.W. Thudichum (1829-1901) as lipids of unknown function and structure.<ref>Thudichum J.L.W.?"A Treatise on the Chemical Constitution of the Balliere" Tindall and Cox, London,?1884</ref> The basic structure is a long-chain base (long-chain amino-alcohol) whose amino-group is acylated with a long-chain fatty acid. This hydrophobic structure is called ceramides.
* ''y'' ... degree of unsaturation
Sphingolipid consists of phospho-sphingolipid and glyco-sphingolipid, whose ceramide structure is bonded with phosphate and (oligo)saccharides, respectively. Phosphosphingolipid includes sphingomyelin, and glycosphingolipid, cerebrosides and gangliosides. Both are abundant in neural tissues.<ref>Gault CR,?Obeid LM,?Hannun YA "An overview of sphingolipid synthesis to breakdown" Adv Exp Med Biol.?2010;688:1-23. PMID 20919643</ref>
* ''z'' ... position of n−''z'' (n minus z; also ω−z or omega-z) nomenclature
* ''w'' ... number of attached sugars (inositol is counted too)
* ''c'' ... serial number
|
|
* ''x'' ... 炭素鎖長
スフィンゴ脂質は J.L.W. Thudichum (1829-1901) により機能や構造未知の脂質として脳から見いだされました。基本骨格は長鎖塩基 (長鎖アミノアルコール) のアミノ基が長鎖脂肪酸とアミド結合したもので、セラミドと呼ばれます。
* ''y'' ... 不飽和度
スフィンゴ脂質はセラミドにリン酸が結合したスフィンゴリン脂質と糖が結合したスフィンゴ糖脂質に分けられます。スフィンゴリン脂質にはスフィンゴミエリンが、スフィンゴ糖脂質にはセレブロシドやガングリオシドなどが含まれ、いずれも神経系に多く存在します。
* ''z'' ... n−''z'' (またはω−zやomega-z)　における数
}}
* ''w'' ... 修飾する糖の個数 (イノシトールも入れる)
 
* ''c'' ... 通し番号
<references/>
 
<!---
{|
|valign="top"|
{| class="wikitable" style="text-align:center"
!width="5%"| code
!colspan="2"| Galactose
|-
| '''0'''
|colspan="2"| no sugar
|-
| '''1'''
|rowspan="3"| <b>Galactose</b><br/>(&alpha; form)
| {{#invoke:LBS|FormatSugar|Gala1-3 ...}}
|-
| '''2''' || {{#invoke:LBS|FormatSugar|Gala1-4 ...}}
|-
| '''3''' || {{#invoke:LBS|FormatSugar|Gala1-6 ...}}
|-
| '''4'''
|rowspan="3"| <b>Galactose</b><br/>(&beta; form)
| {{#invoke:LBS|FormatSugar|Galb1-3 ...}}
|-
| '''5''' || {{#invoke:LBS|FormatSugar|Galb1-4 ...}}
|-
| '''6''' || {{#invoke:LBS|FormatSugar|Galb1-6 ...}}
|}
|valign="top"|
{| class="wikitable" style="text-align:center"
!width="5%"| code
!colspan="2"| ''N''-Acetylated Sugars
|-
|-
| '''7'''
|rowspan="3"| <b>''N''-Acetyl Galactosamine</b><br/>(&beta; form)
| {{#invoke:LBS|FormatSugar|GalNAcb1-3 ...}}
|-
| '''8''' || {{#invoke:LBS|FormatSugar|GalNAcb1-4 ...}}
|-
| '''9''' || {{#invoke:LBS|FormatSugar|GalNAcb1-6 ...}}
|-
| '''A'''
|rowspan="3"| <b>''N''-Acetyl Glucosamine</b><br/>(&beta; form)
| {{#invoke:LBS|FormatSugar|GlcNAcb1-3 ...}}
|-
| '''B'''
| {{#invoke:LBS|FormatSugar|GlcNAcb1-4 ...}}
|-
| '''C'''
| {{#invoke:LBS|FormatSugar|GlcNAcb1-6 ...}}
|}
|}
 
 
{|
|valign="top"|
{| class="wikitable" style="text-align:center"
!width="5%"| code
!colspan="2"| Galactose & Glucose
|-
| '''D'''
|rowspan="2"| <b>Aminated Sugars</b><br/>(Except for Code 7&sim;C)
| {{#invoke:LBS|FormatSugar|GalNAc, GalN}}
|-
| '''E''' || {{#invoke:LBS|FormatSugar|GlcNAc, GlcN}}
|-
| '''F'''
| <b>Galactose</b><br/>(Except Code 1&sim;6)
| <span style="color:gold"><b>Gal</b></span>
|-
| '''G'''
| <b>Glucose</b>
| <span style="color:blue"><b>Glc</b></span>
|}
|valign="top"|
{| class="wikitable" style="text-align:center"
!width="5%"| code
! Other Sugars
|-
| '''J''' || Inositol (<span style="color:"><b>Ins</b></span>)
|-
| '''K''' || Fucose (<span style="color:red"><b>Fuc</b></span>)
|-
| '''L''' || Pentose sugars<br/>(<span style="color:DarkOrange"><b>Ara, Xyl</b></span>)
|-
| '''M''' || Mannose and Rhamnose (= 6-deoxymannose)<br/>(<span style="color:green"><b>Man, Rha</b></span>)
|-
| '''N''' || Sialic acids<br/>(<b><span style="color:Purple">NeuAc, NeuNH</span>, <span style="color:gray">NeuGc</span>, <span style="color:Green">Kdn</span></b>)
|}
|}
 
{|
|valign="top"|
{| class="wikitable" style="text-align:center"
!width="5%"| code
!colspan="2"| Modifiers
|-
| '''P''' || Phosphate (<b>HPO4</b>), Sulphate (<b>HSO4</b>),<br/>and Phosphocholine (<b>PC</b>)
|-
| '''Q''' || Aminoethylphosphates<br/><b>AEPn, MAEPn, MAEPr, EtnP</b>
|-
| '''R''' || Alkyl and acyl groups<br/><b>OAc, Methyl, Butenyl</b>
|}
|valign="top"|
{| class="wikitable" style="text-align:center"
!width="5%"| code
!colspan="2"| Abbreviations
|-
| '''Y''' || {{#invoke:LBS|FormatSugar|GlcNAcb1-3Manb1-4Glcb1-1Cer}}
|-
| '''Z''' || {{#invoke:LBS|FormatSugar|Galb1-4Glcb1-1bCer}}
|}
|}
 
 
 
==={{Bilingual|よく知られたパターン|Common Patterns}}===
 
{| class="wikitable"
! Common Name || Records || Sequence
|-
|colspan="3" style="background:#efefef; text-align:center"| By GalCer Synthase (EC 2.4.1.62)
{{#repeat:LBS/AbbrevTable/Row|1|
Gala_(Ga) Gala1-4/6Galb1-Cer LBSF%5b23%5d.
Spirometo_(Sp) Galb1-4Glcb1-3Galb1-Cer LBSFG5
}}
|-
|colspan="3" style="background:#efefef; text-align:center"| By GlcCer Synthase (EC 2.4.1.80)
{{#repeat:LBS/AbbrevTable/Row|1|
Ganglio_(Gg) GalNAcb1-4Galb1-4Glcb1-Cer LBSZ8.
Isoganglio_(iGg) GalNAcb1-3Galb1-4Glcb1-Cer LBSZ7.
Globo_(Gb) Gala1-4Galb1-4Glcb1-Cer LBSZ2.
Isoglobo_(iGb) Gala1-3Galb1-4Glcb1-Cer LBSZ1.
Lacto_(Lc) Galb1-3GlcNAcb1-3Galb1-4Glcb1-Cer LBSZD4
NeoLacto_(nLc) Galb1-4GlcNAcb1-3Galb1-4Glcb1-Cer LBSZA5
Muco_(Mc) Galb1-4Galb1-4Glcb1-Cer LBSZ5.
}}
|-
|colspan="3" style="background:#efefef; text-align:center"| With Mannose
{{#repeat:LBS/AbbrevTable/Row|1|
Arthro_(At) GlcNAcb1-3Manb1-4Glcb1-Cer LBSY
Mollu_(Mu) Mana1-3Manb1-4Glcb1-Cer LBSGMM
}}
}}
|}
==={{Bilingual|分類|Classification}}===
===={{Bilingual|糖の個数|By the Number of Sugars}}====
{| class="wikitable" border="1" cellpadding="2" cellspacing="1" margin: 1em 1em 1em 1em"
|+ Table 1. Classification by the Number of Sugars
! # of sugars || {{Bilingual|脊椎動物 (V)|'''V'''ertebrate}} ({{#expr:{{#countTitle:LBS.....V}}+{{#countTitle:LBS.....N}}}} items) || {{Bilingual|無脊椎動物 (I)|'''I'''nvertebrate}} ({{#expr:{{#countTitle:LBS.....I}}+{{#countTitle:LBS.....N}}}} items)
|- valign="top"
| 1 || {{MapLink|ListMol|LBS...01V|LBS...01V}} || {{MapLink|ListMol|LBS...01I|LBS...01I}}
|-
| 2 || {{MapLink|ListMol|LBS...02V|LBS...02V}} || {{MapLink|ListMol|LBS...02I|LBS...02I}}
|-
| 3 || {{MapLink|ListMol|LBS...03V|LBS...03V}} || {{MapLink|ListMol|LBS...03I|LBS...03I}}
|-
| 4 || {{MapLink|ListMol|LBS...04V|LBS...04V}} || {{MapLink|ListMol|LBS...04I|LBS...04I}}
|-
| 5 || {{MapLink|ListMol|LBS...05V|LBS...05V}} || {{MapLink|ListMol|LBS...05I|LBS...05I}}
|-
| 6 || {{MapLink|ListMol|LBS...06V|LBS...06V}} || {{MapLink|ListMol|LBS...06I|LBS...06I}}
|-
| 7 || {{MapLink|ListMol|LBS...07V|LBS...07V}} || {{MapLink|ListMol|LBS...07I|LBS...07I}}
|-
| 8 || {{MapLink|ListMol|LBS...08V|LBS...08V}} || {{MapLink|ListMol|LBS...08I|LBS...08I}}
|-
| 9 || {{MapLink|ListMol|LBS...09V|LBS...09V}} || {{MapLink|ListMol|LBS...09I|LBS...09I}}
|-
| 10-19 || {{MapLink|ListMol|LBS...1.V|LBS...1.<VN>}} || {{MapLink|ListMol|LBS...1.I|LBS...1.<IN>}}
|-
| 20-29 || {{MapLink|ListMol|LBS...2.V|LBS...2.<VN>}} || {{MapLink|ListMol|LBS...2.I|LBS...2.<IN>}}
|}
===={{Bilingual|シアル酸の個数|By the Number of Sialic acids}}====
{| class="wikitable" border="1" cellpadding="2" cellspacing="1" margin: 1em 1em 1em 1em"
|+ Table 2. Classification by the Number of Sialic acids
! # of sialic acids || {{Bilingual|脊椎動物 (V)|'''V'''ertebrate}} ({{#expr:{{#countTitle:LBS.....V}}+{{#countTitle:LBS.....N}}}} items) || {{Bilingual|無脊椎動物 (I)|'''I'''nvertebrate}} ({{#expr:{{#countTitle:LBS.....I}}+{{#countTitle:LBS.....N}}}} items)
|- valign="top"
| 1 || {{MapLink|ListMol|LBS.....V1|LBS.....V1}} || {{MapLink|ListMol|LBS.....I1|LBS.....I1}}
|-
| 2 || {{MapLink|ListMol|LBS.....V2|LBS.....V2}} || {{MapLink|ListMol|LBS.....I2|LBS.....I2}}
|-
| 3 || {{MapLink|ListMol|LBS.....V3|LBS.....V3}} || {{MapLink|ListMol|LBS.....I3|LBS.....I3}}
|-
| 4 || {{MapLink|ListMol|LBS.....V4|LBS.....V4}} || {{MapLink|ListMol|LBS.....I4|LBS.....I4}}
|-
| 5 || {{MapLink|ListMol|LBS.....V5|LBS.....V5}} || {{MapLink|ListMol|LBS.....I5|LBS.....I5}}
|-
| 6 || {{MapLink|ListMol|LBS.....V6|LBS.....V6}} || {{MapLink|ListMol|LBS.....I6|LBS.....I6}}
|-
| 7 || {{MapLink|ListMol|LBS.....V7|LBS.....V7}} || {{MapLink|ListMol|LBS.....I7|LBS.....I7}}
|-
| 8 || {{MapLink|ListMol|LBS.....V8|LBS.....V8}} || {{MapLink|ListMol|LBS.....I8|LBS.....I8}}
|}
--->

Latest revision as of 01:15, 26 May 2023

Sphingolipid


Upper classes: LB

Class Overview

Three Sphingolipid categories (LBS) exist in this database.

このデータベースではスフィンゴ脂質を以下に分けています。

Ceramide
| OH
(C14-chain)＝／＼／ーOH
(fatty acid) ー | NH

セラミド 		Glycosphingolipid
| OH
(C14-chain)＝／＼／ーO-(sugar)
(fatty acid) ー | NH

スフィンゴ糖脂質 		Phosphosphingolipid
| OH
(C14-chain)＝／＼／ーO-(phosphate)
(fatty acid) ー | NH

スフィンゴリン脂質

Go to Sphingolipid search.


Sphingolipid

Notation

Page/ID-Code Design

Major series of phosphosphingolipids are determined by molecules bound to their phosphates, and the series of glycosphingolipids are determined by oligosaccharides bound to their ceramides. The IUPAC series of glycosphingolipids (1977) were based on the order and bonding patterns of four sugars rooting at the long-chain base. Our series, however, are based on three sugars. Two original series, Echino and Schisto, are also added.

スフィンゴリン脂質はリン酸に結合する分子や糖の種類、スフィンゴ糖脂質はセラミドに結合する糖鎖により系列を作成しています。1977年にIUPACが提唱したスフィンゴ糖脂質の系列は、長鎖塩基に結合する四糖の並びと結合を基準にしています。ここではより広い糖鎖の系列を検索できるよう、三糖を基準に分類しています。また新たにEchinoとSchistoの系列を加えています。

L B S G/P s1 s2 n1 n2 y c1 c2
 
G/P G (glyco) P (phospho)
s1, s2 structure code as explained below
n1, n2 number of sugars (2 digits)
y number of sialic acids (1 digit)
c1, c2 serial numbers

First (s1) Digit for Glycosphingolipid

First sugar Code Root sequence Major Series
Cerebroside For GalCer and GlcCer, visit this page.
starting with
Galactose

(
) 		Gal-Cer
Galα1-4/6Galβ1-Cer
Galβ1-4Glcβ1-3Galβ1-Cer
starting with
Glucose

(
) 		GalNAcβ-Galβ-Glcβ-Cer
GalNAcβ1-4Galβ1-4Glcβ1-Cer
[1] 		GalNAcβ1-3Galβ1-4Glcβ1-Cer
GlcNAcβ1-3(GalNAcβ1-4)Galβ1-4Glcβ1-Cer
GalNAcβ1-4(NeuAcα2-3)Galβ1-4Glcβ1-Cer
GalNAcβ1-4(NeuAcα2-8NeuAcα2-3)Galβ1-4Glcβ1-Cer
GalNAcβ1-4(NeuAcα2-8NeuAcα2-8NeuAcα2-3)Galβ1-4Glcβ1-Cer
...(NeuAcα2-6)GalNAcβ1-4Galβ1-4Glcβ1-Cer
...(NeuAcα2-8NeuAcα2-6)GalNAcβ1-4Galβ1-4Glcβ1-Cer

(
) 		GlcNAcβ-Galβ-Glcβ-Cer
Galβ1-3GlcNAcβ1-3Galβ1-4Glcβ1-Cer
[2] 		Galβ1-4GlcNAcβ1-3Galβ1-4Glcβ1-Cer

(
) 		Galα-Galβ-Glcβ-Cer
Galα1-4Galβ1-4Glcβ1-Cer
[1] 		Galα1-3Galβ1-4Glcβ1-Cer

(
) 		Gal-Glc-Cer
(Other than G2∼G4)
Galβ1-4Galβ1-4Glcβ1-Cer

(
) 		Man-Glcβ-Cer
GlcNAcβ1-3Manβ1-4Glcβ1-Cer
Manα1-3Manβ1-4Glcβ1-Cer

(
) 		NeuAc/NeuGc-Glcβ-Cer
NeuGc or NeuAcα2-6Glcβ1-Cer

(
) 		GalNAc-Glc-Cer
[3] 		GalNAcβ1-4Glcβ1-Cer
starting with
Other Sugars
Symbols follow the Sugar-digit table.
  1. ↑ 1.0 1.1 In IUPAC, "iso" refers to a change from position 4 to position 3.
  2. ↑ In IUPAC, "neo" refers to a change from position 3 to position 4.
  3. ↑ Makaaru CK, Damian RT, Smith DF, Cummings RD. "The human blood fluke Schistosoma mansoni synthesizes a novel type of glycosphingolipid" J Biol Chem 1992 267:2251-2257 PMID 1733932

First (s1) Digit for Phosphosphingolipid

First sugar Code Root sequence Major Series
No Sugar Attached P1 (LBSP) R-P-Cer Sphingomyelin and Ceramide phosphoetanolamine
(Visit this page.)
starting with
Inositol

(29 items) 		GlcNα/β1−2/6Ins1-P-Cer
GlcNα/β1-2/6Ins1-P-Cer

(10 items) 		GlcAα/β1−2/6Ins1-P-Cer
GlcAα/β1-2/6Ins1-P-Cer

(52 items) 		Manα/β1−2/6Ins1-P-Cer
Manα/β1-2/6Ins1-P-Cer

(21 items) 		Gal, Glc, and Others X-Ins1-P-Cer

Second (s2) Digit

Click to see the full list. For abbreviations, see #Notation.

Code Structure
A Glc LBS-Monomer-Glc.png
B Gal LBS-Monomer-Gal.png
C GlcNAc LBS-Monomer-GlcNAc.png
D GalNAc LBS-Monomer-GalNAc.png
E GlcN LBS-Monomer-GlcN.png
F GalN LBS-Monomer-GalN.png
G GlcA LBS-Monomer-GlcA.png
H GalA LBS-Monomer-GalA.png
I not used
Code Structure
J
LBS-Monomer-Man.png
K
LBS-Monomer-Rha.png
L
M Fucose (
,
,
) LBS-Monomer-Fuc.png
N
LBS-Monomer-Ara.png
O
LBS-Monomer-Xyl.png
P
LBS-Monomer-NeuAc.png
Q
LBS-Monomer-NeuGc.png
R
LBS-Monomer-KDN.png
Code Structure
S
LBS-Monomer-P.png
T
,
,
LBS-Monomer-AEPn.png
U
LBS-Monomer-S.png
V acyl/alkyl/alkenyl chain LBS-Monomer-Alkyl.png

Biosynthesis

Sphingosine is synthesized from decarboxylating condensation of palmitoyl CoA with serine on the ER membrane. It is a 18-carbon amino alcohol (16 carbons from palmitic acid and 2 from serine) with one unsaturated bond (trans-form) at the C-4 position (2-amino-4-octadecene-1,3-diol). (more details)

スフィンゴシンはパルミトイルCoAがアミノ酸セリンと脱炭酸縮合して生成します。炭素を18個含むアミノアルコール(16個がパルミチン酸、2個がセリン由来)でトランス型の不飽和結合をC-4に1つ含みます。（詳細はこちら）


History of Sphingolipids

Sphingolipids were first isolated from brain by J.L.W. Thudichum (1829-1901) as lipids of unknown function and structure.[1] The basic structure is a long-chain base (long-chain amino-alcohol) whose amino-group is acylated with a long-chain fatty acid. This hydrophobic structure is called ceramides. Sphingolipid consists of phospho-sphingolipid and glyco-sphingolipid, whose ceramide structure is bonded with phosphate and (oligo)saccharides, respectively. Phosphosphingolipid includes sphingomyelin, and glycosphingolipid, cerebrosides and gangliosides. Both are abundant in neural tissues.[2]

スフィンゴ脂質は J.L.W. Thudichum (1829-1901) により機能や構造未知の脂質として脳から見いだされました。基本骨格は長鎖塩基 (長鎖アミノアルコール) のアミノ基が長鎖脂肪酸とアミド結合したもので、セラミドと呼ばれます。 スフィンゴ脂質はセラミドにリン酸が結合したスフィンゴリン脂質と糖が結合したスフィンゴ糖脂質に分けられます。スフィンゴリン脂質にはスフィンゴミエリンが、スフィンゴ糖脂質にはセレブロシドやガングリオシドなどが含まれ、いずれも神経系に多く存在します。

  1. ↑ Thudichum J.L.W.?"A Treatise on the Chemical Constitution of the Balliere" Tindall and Cox, London,?1884
  2. ↑ Gault CR,?Obeid LM,?Hannun YA "An overview of sphingolipid synthesis to breakdown" Adv Exp Med Biol.?2010;688:1-23. PMID 20919643


Subcategories

This category has the following 4 subcategories, out of 4 total.

L

Retrieved from "http://lipidbank.jp/mediawiki/index.php?title=Category:LBS&oldid=117167"