Category:LBS: Difference between revisions

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{| style="float:right"
{| style="float:left"
| __TOC__
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==Class Overview==
=={{Bilingual|概要|Class Overview}}==


The Sphingolipid category (LBS) in the database includes phosphosphingolipid and glycosphingolipid.
{{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"
{|  
|-
|-
! colspan="3" | Sphingolipid Overview
| style="vertical-align:top" width="33%"|
[[:Category:LBSB| '''Ceramide''']]<br/>{{LBS/Cer|OH}}<br/><small>セラミド</small>
| style="vertical-align:top" width="33%"|
[[:Category:LBSG| '''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>
|-
|-
| align="center" style="vertical-align:top" width="33%"|
|
[[:Category:LBSP|Phosphosphingolipid]]<br/>(including GIPC)
*[[:Category:LBSB|Ceramide and long chain bases]]
<br>[[Image:LBSPP.png|120px]]<br/><small>スフィンゴリン脂質 (GIPC含む)</small>
|
| align="center" style="vertical-align:top" width="33%"|
*[[:Category:LBSC|Cerebroside <small>(monohexosyl ceramides)</small>]]
[[:Category:LBSG|Glycosphingolipid]]
*[[:Category:LBSG|Glycosylceramide <small>(polyhexosyl ceramides)</small>]]
<br/>[[Image:LBSnn.png|120px]]<br/><small>スフィンゴ糖脂質</small>
|
* [[:Category:LBSC|Cerebroside <small>セレブロシド (n = 1)</small>]]
*[[:Category:LBSP|Sphingomyelins and GIPC]]
* [[:Category:LBSG|Glycosylceramide <small>(n > 1)</small>]]
|}
|}
</center>
</center>


==={{Bilingual|スフィンゴシンとセラミド|Sphingosine & Ceramide}}===
{{Twocolumn|
Sphingolipids were first isolated from brain by J.L.W. Thudichum (1829-1901) as lipids of unknown function and structure. The name "sphingo" comes from the Greek word ''sphingein'' for holding tight. (The Sphinx also comes from this word root. See the Wikipedia article for [http://en.wikipedia.org/wiki/Sphinx Sphinx], as well as sphincter muscle.) The basic structure is a long-chain base, usually sphingosine (2-amino-4-octadecene-1,3-diol abbreviated as d18:1), whose amino-group is acylated with a long-chain fatty acid. This hydrophobic structure is called ceramides.
|
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。スフィンゴという名前はギリシャ語の sphingein に由来しており、「固く縛る」という意味です。(スフィンクスの語源もこれに同じで、括約筋のことを英語で sphincter muscle といいます。)基本骨格は長鎖塩基 (長鎖アミノアルコール、通常はd18:1と記載されるスフィンゴシン) 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。
}}
{{Twocolumn|
Ceramides with the sphingoid are prevalent as membrane components of eukaryotic cells. Sphingomyelin is a ceramide with phosphocholine. Some ceramides are organ-specific.
|
スフィンゴ骨格をもつセラミドは細胞組織の膜成分として普遍的に存在します。セラミドにホスホコリンがついたものがスフィンゴミエリンです。臓器特異的なセラミドもあります。
}}
<!----
<center>
<center>
{| class="wikitable"
{| 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.}}]]
|colspan="3"| Glycosylceramides
</big>
|colspan="3"| Glycosyl inositol phosphorylceramides (GIPCs)
|-
|
|Fatty acid
|LCB
|Ref.
|Fatty acid
|LCB
|Ref.
|-
|Plant
| h[C16:0 -C26:0] <br/> h[C16:1 -C26:1] <br/> h[C16:0] <br/> h[VLCFA]
| d18:2 <br/> d18:2 <br/> d18:1 <br/> t18:1
| 1,3<br/>1,3<br/>1<br/>1,3
| h[VLCFA] <br/> h[C14:0-C26:0] <br/> h[C20:1-C26:1]
| t18:1 <br/> t18:0/1 <br/> t18:0/1
| 1 <br/> 4 <br/> 1,4
|-
|Fungi
| h[C16:0 - C18:0] <br/> h[C16:1- C18:1]
| 9-methyl d18:2 <br/> 9-methyl d18:2
| 2,3<br/>2,3
| C24:1 - C26:1 <br/> h[C24:0 - C26:0] <br/>  h[C16:0 - C26:0]
| t18:0 <br/> t18:0 <br/> t18:0, t20:0
| 2 <br/> 3 <br/> 3,4
|}
|}
<small>LCB: long chain base, h: hydroxy, VLCFA: very long chain fatty acid</small>
</center>
</center>
--->
<references/>


==Biosynthesis==
==={{Bilingual|スフィンゴ脂質の歴史|History of Sphingolipids}}===
{{Twocolumn|
{{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]])
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.
Sphingolipid consists of phospho-sphingolipid and glyco-sphingolipid, whose ceramide structure is bonded with phosphate and (poly)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>
|
|
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]])
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。
}}
}}


==Sphingolipid スフィンゴ脂質==
<references/>
 
=={{Bilingual|スフィンゴ脂質|Sphingolipid}}==


===Notation===
==={{Bilingual|表記法|Notation}}===
{| class="wikitable collapsible collapsed" style="width:80%"
{| 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"| Symbol Abbreviations (e.g. Glc = glucose)
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!colspan="4" align="center" style="background:lightgray"| Backbones
!colspan="4" align="center" style="background:lightgray"| Backbones
{{#repeatnum:LBS/AbbrevRow|1|
{{#repeatnum:LBS/AbbrevRow|1|
Cer && ceramide && セラミド
Cer && ceramide && セラミド &&
Sph && sphingosine && スフィンゴシン
Sph && sphingosine && スフィンゴシン &&
}}
}}
|-
|-
!colspan="4" align="center" style="background:lightgray"| Sugars
!colspan="4" align="center" style="background:lightgray"| Sugars
{{#repeatnum:LBS/AbbrevRow|1|
{{#repeatnum:LBS/AbbrevRow|1|
Glc && glucose && グルコース
Glc && glucose && グルコース && C6H12O6 &&
Gal && galactose && ガラクトース
Gal && galactose && ガラクトース && C6H12O6 &&
GlcNAc && ''N''-acetyl-glucosamine && ''N''-アセチルグルコサミン
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
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
GlcN && glucosamine && グルコサミン && C6H13NO5
GalN && galactosamine && ガラクトサミン
GalN && galactosamine && ガラクトサミン && C6H13NO5
GlcA && glucuronic acid && グルクロン酸
GlcA && glucuronic acid && グルクロン酸 && C6H10O7
GalA && galacturonic acid && ガラクツロン酸
GalA && galacturonic acid && ガラクツロン酸 && C6H10O7 &&
Man && mannose && マンノース
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)
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
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)
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
Ara && arabinose && アラビノース && C5H10O5 && 5460291
Xyl && xylose && キシロース
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)
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
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
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
Kdn && 2-keto-3-deoxy-D-glycero-<br/>D-galacto-nononic acid && デアミノノイラミン酸 && C9H16O9 && 13991616
}}
}}
|-
|-
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==={{Bilingual|分類体系 |Page/ID-Code Design}}===
==={{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 polysaccharides 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。
}}


{|
{|
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|}
|}


===First (s1) Code for Glycosphingolipid===
==={{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"
{| class="wikitable" style="text-align:right; background-color:white"
! First sugar || Code || Root sequence
! First sugar || Code || Root sequence
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|
{| style="width:100%;"
{| style="width:100%;"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gala1-4?6?Galb1-Cer|Gala]]
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gala1-4?6?Galb1-Cer|Gala / Neogala]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Gala1-4/6Galb1-Cer}}  
|style="border:0;text-align:right"| {{LBS/FormatSugar|Gala1-4/6Galb1-Cer}}  
|-
|-
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|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4Galb1-4Glcb1-Cer}}
|-
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAcb1-3Galb1-4Glcb1-Cer|Isoganglio]]<ref name="iso">"iso" refers to a change from position 4 to position 3.</ref>
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAcb1-3Galb1-4Glcb1-Cer|Isoganglio]]<ref name="iso">In IUPAC, "iso" refers to a change from position 4 to position 3.</ref>
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-3Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-3Galb1-4Glcb1-Cer}}
|-
|-
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|-
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*\(?NeuAca2-3\)?Galb1-4Glcb1-Cer|a-series]]
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*\(?NeuAca2-3\)?Galb1-4Glcb1-Cer|a-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|(NeuAca2-3)Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*\(?NeuAca2-8NeuAca2-3\)?Galb1-4Glcb1-Cer|b-series]]
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*\(?NeuAca2-8NeuAca2-3\)?Galb1-4Glcb1-Cer|b-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|(NeuAca2-8NeuAca2-3)Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-8NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*\(?NeuAca2-8NeuAca2-8NeuAca2-3\)?Galb1-4Glcb1-Cer|c-series]]
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*\(?NeuAca2-8NeuAca2-8NeuAca2-3\)?Galb1-4Glcb1-Cer|c-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|(NeuAca2-8NeuAca2-8NeuAca2-3)Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4(NeuAca2-8NeuAca2-8NeuAca2-3)Galb1-4Glcb1-Cer}}
|-
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*\(?NeuAca2-6\)?GalNAcb1-4Galb1-4Glcb1-Cer|&alpha;-series]]
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*\(?NeuAca2-6\)?GalNAcb1-4Galb1-4Glcb1-Cer|&alpha;-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|(NeuAca2-6)GalNAcb1-4Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{LBS/FormatSugar|...(NeuAca2-6)GalNAcb1-4Galb1-4Glcb1-Cer}}
|-
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*\(?NeuAca2-8NeuAca2-6\)?GalNAcb1-4Galb1-4Glcb1-Cer|&beta;-series]]
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Structure.*\(?NeuAca2-8NeuAca2-6\)?GalNAcb1-4Galb1-4Glcb1-Cer|&beta;-series]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|(NeuAca2-8NeuAca2-6)GalNAcb1-4Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{LBS/FormatSugar|...(NeuAca2-8NeuAca2-6)GalNAcb1-4Galb1-4Glcb1-Cer}}
|}
|}
|-
|-
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|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-3GlcNAcb1-3Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-3GlcNAcb1-3Galb1-4Glcb1-Cer}}
|-
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gal.1-4GlcNAcb1-3Galb1-4Glcb1-Cer|Neolacto]]<ref name="neo">"neo" refers to a change from position 3 to position 4.</ref>
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Gal.1-4GlcNAcb1-3Galb1-4Glcb1-Cer|Neolacto]]<ref name="neo">In IUPAC, "neo" refers to a change from position 3 to position 4.</ref>
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-4GlcNAcb1-3Galb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{LBS/FormatSugar|Galb1-4GlcNAcb1-3Galb1-4Glcb1-Cer}}
|}
|}
|-
|-
| [[Volatile:ListMol/LBS|LBSG4|'''G4''']] <br/> ([[Volatile:ClassMatrix|LBSG4.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG4}} items]])
| [[Volatile:ListMol/LBStitle|LBSG4|'''G4''']] <br/> ([[Volatile:ClassMatrix|LBSG4.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|{{#countTitle:LBSG4}} items]])
|style="text-align:right"| '''Gal<sub>&alpha;</sub>'''-Gal<sub>&beta;</sub>-Glc<sub>&beta;</sub>-Cer
|style="text-align:right"| '''Gal<sub>&alpha;</sub>'''-Gal<sub>&beta;</sub>-Glc<sub>&beta;</sub>-Cer
|
|
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|-
|-
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Mana1-3Manb1-4Glcb1-Cer|Mollu]]
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*Mana1-3Manb1-4Glcb1-Cer|Mollu]]
|style="border:0;text-align:right"| {{LBS/FormatSugar|Mana1-3Manb1-4Glcb1.Cer}}
|style="border:0;text-align:right"| {{LBS/FormatSugar|Mana1-3Manb1-4Glcb1-Cer}}
|}
|}
|-
|-
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{| style="width:100%"
{| style="width:100%"
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAc.1-4Glc.1-Cer|Plathy]]
|style="border:0;text-align:left"| [[Volatile:ListMol/LBS|Mainchain.*GalNAc.1-4Glc.1-Cer|Schisto]]<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"| {{LBS/FormatSugar|GalNAcb1-4Glcb1-Cer}}
|style="border:0;text-align:right"| {{LBS/FormatSugar|GalNAcb1-4Glcb1-Cer}}
|}
|}
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| [[Volatile:ListMol/LBStitle|LBSG(A~B~C~D~E~F~G~H~J~K~M~N~O~P~Q~R)|'''G'''('''A'''&sim;'''R''')]]
| [[Volatile:ListMol/LBStitle|LBSG(A~B~C~D~E~F~G~H~J~K~M~N~O~P~Q~R)|'''G'''('''A'''&sim;'''R''')]]
|colspan="2"| Symbols follow the Sugar-digit table.
|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  
! First sugar || Code || Root sequence  
!colspan="2"| Major Series
!colspan="2"| Major Series
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| '''P1''' ([[:Category:LBSP|LBSP]])
| '''P1''' ([[:Category:LBSP|LBSP]])
| R-P-Cer
| R-P-Cer
| Sphingomyelin and Phosphoetanolamine-ceramide<br/>(Visit [[:Category:LBSP|this page]].)
| Sphingomyelin and Ceramide phosphoetanolamine<br/>(Visit [[:Category:LBSP|this page]].)
|-
|-
! rowspan="4" | starting with<br/><big>Inositol</big>
! rowspan="4" | starting with<br/><big>Inositol</big>
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|}
|}


<references/>
==={{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]].


===Second (s2) Code for subsequent sugars===
{|  
 
{{Bilingual|記号の略称については|For abbreviations, see}} [[#Notation]].
 
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| acyl/alkyl/alkenyl chain [[File:LBS-Monomer-Alkyl.png]]
| acyl/alkyl/alkenyl chain [[File:LBS-Monomer-Alkyl.png]]
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=={{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]])
}}





Revision as of 05:54, 22 May 2018

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)OH
(fatty acid) ー | NH

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

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

スフィンゴリン脂質

Go to Sphingolipid search.

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 (poly)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

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 polysaccharides 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
LBSG1|G1
(LBSG1.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|79 items)
Gal-Cer
Mainchain.*Gala1-4?6?Galb1-Cer|Gala / Neogala Galα1-4/6Galβ1-Cer
Mainchain.*Galb1-4Glcb1-3Galb1-Cer|Spirometo Galβ1-4Glcβ1-3Galβ1-Cer
starting with
Glucose
LBSG2|G2
(LBSG2.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|88 items)
GalNAcβ-Galβ-Glcβ-Cer
Mainchain.*GalNAcb1-4Galb1-4Glcb1-Cer|Ganglio GalNAcβ1-4Galβ1-4Glcβ1-Cer
Mainchain.*GalNAcb1-3Galb1-4Glcb1-Cer|Isoganglio[1] GalNAcβ1-3Galβ1-4Glcβ1-Cer
Structure.*GlcNAcb1-3\(.*GalNAcb1-4\)Galb1-4Glcb1-Cer|Lactoganglio GlcNAcβ1-3(GalNAcβ1-4)Galβ1-4Glcβ1-Cer
Structure.*\(?NeuAca2-3\)?Galb1-4Glcb1-Cer|a-series GalNAcβ1-4(NeuAcα2-3)Galβ1-4Glcβ1-Cer
Structure.*\(?NeuAca2-8NeuAca2-3\)?Galb1-4Glcb1-Cer|b-series GalNAcβ1-4(NeuAcα2-8NeuAcα2-3)Galβ1-4Glcβ1-Cer
Structure.*\(?NeuAca2-8NeuAca2-8NeuAca2-3\)?Galb1-4Glcb1-Cer|c-series GalNAcβ1-4(NeuAcα2-8NeuAcα2-8NeuAcα2-3)Galβ1-4Glcβ1-Cer
Structure.*\(?NeuAca2-6\)?GalNAcb1-4Galb1-4Glcb1-Cer|α-series ...(NeuAcα2-6)GalNAcβ1-4Galβ1-4Glcβ1-Cer
Structure.*\(?NeuAca2-8NeuAca2-6\)?GalNAcb1-4Galb1-4Glcb1-Cer|β-series ...(NeuAcα2-8NeuAcα2-6)GalNAcβ1-4Galβ1-4Glcβ1-Cer
LBSG3|G3
(LBSG3.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|173 items)
GlcNAcβ-Galβ-Glcβ-Cer
Mainchain.*Galb1-3GlcNAcb1-3Galb1-4Glcb1-Cer|Lacto Galβ1-3GlcNAcβ1-3Galβ1-4Glcβ1-Cer
Mainchain.*Gal.1-4GlcNAcb1-3Galb1-4Glcb1-Cer|Neolacto[2] Galβ1-4GlcNAcβ1-3Galβ1-4Glcβ1-Cer
LBSG4|G4
(LBSG4.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|55 items)
Galα-Galβ-Glcβ-Cer
Mainchain.*Gala1-4Galb1-4Glcb1-Cer|Globo Galα1-4Galβ1-4Glcβ1-Cer
Mainchain.*Gala1-3Galb1-4Glcb1-Cer|Isoglobo[1] Galα1-3Galβ1-4Glcβ1-Cer
LBSG5|G5
(LBSG5.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|113 items)
Gal-Glc-Cer
(Other than G2∼G4)
Mainchain.*Galb1-4Galb1-4Glcb1-Cer|Muco Galβ1-4Galβ1-4Glcβ1-Cer
LBSG6|G6
(LBSG6.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|68 items)
Man-Glcβ-Cer
Mainchain.*GlcNAcb1-3Manb1-4Glcb1-Cer|Arthro GlcNAcβ1-3Manβ1-4Glcβ1-Cer
Mainchain.*Mana1-3Manb1-4Glcb1-Cer|Mollu Manα1-3Manβ1-4Glcβ1-Cer
LBSG7|G7
(LBSG7.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|21 items)
NeuAc/NeuGc-Glcβ-Cer
Mainchain.*Neu(A~G)c.2-6Glcb1-Cer|Echino NeuGc or NeuAcα2-6Glcβ1-Cer
LBSG8|G8
(LBSG8.....|7|8|9|9|Number_of_Sugars|Number_of_Sialic_acids|12 items)
GalNAc-Glc-Cer
Mainchain.*GalNAc.1-4Glc.1-Cer|Schisto[3] GalNAcβ1-4Glcβ1-Cer
starting with
Other Sugars
LBSG(A~B~C~D~E~F~G~H~J~K~M~N~O~P~Q~R)|G(AR) 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
LBSP2|P2
(29 items)
GlcNα/β1−2/6Ins1-P-Cer
Mainchain.*GlcN.1-.Ins-P-Cer|Protozoa & Fungi-specific GlcNα/β1-2/6Ins1-P-Cer
LBSP3|P3
(10 items)
GlcAα/β1−2/6Ins1-P-Cer
Mainchain.*GlcA.1-.Ins-P-Cer|Plant-specific GlcAα/β1-2/6Ins1-P-Cer
LBSP4|P4
(52 items)
Manα/β1−2/6Ins1-P-Cer
Mainchain.*Man.1-.Ins-P-Cer|Fungi-specific Manα/β1-2/6Ins1-P-Cer
LBSP5|P5
(21 items)
Others 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 Structure.*Man|Mannose LBS-Monomer-Man.png
K Structure.*Rha|Rhamnose LBS-Monomer-Rha.png
L %53%74%72%75%63%74%75%72%65%2e%2A%49%6e%73%28%4d%65%29%3F%2d%50%2d%5B%5E%43%65%72%5D|Inositol
M Fucose (%53%74%72%75%63%74%75%72%65%5B%5E%46%5D%2B%46%75%63%5B%5E%46%5D%2B%24| 1, %53%74%72%75%63%74%75%72%65%28%5B%5E%46%5D%2B%46%75%63%29%7B%32%7D%5B%5E%46%5D%2B%24|2, %53%74%72%75%63%74%75%72%65%28%5B%5E%46%5D%2B%46%75%63%29%7B%33}|>3) LBS-Monomer-Fuc.png
N Structure.*Ara|Arabinose LBS-Monomer-Ara.png
O Structure.*Xyl|Xylose LBS-Monomer-Xyl.png
P Structure.*(NeuAc~NeuNH)|NeuAc / NeuNH LBS-Monomer-NeuAc.png
Q Structure.*(NeuGc)|NeuGc LBS-Monomer-NeuGc.png
R Structure.*(KDN)|Kdn LBS-Monomer-KDN.png
Code Structure
S Structure.*(Phospho)|Phosphate (except GIPC) LBS-Monomer-P.png
T Structure.*(AEPn)|(M)AEPn, Structure.*(EtnP)|EtnP, Structure.*(PC)|PC LBS-Monomer-AEPn.png
U Structure.*Sulfo|Sulfate 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


Subcategories

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