Category:LBS

Sphingolipid


Upper classes: LB

Class Overview

The Sphingolipid category (LBS) in this database includes phosphosphingolipid and glycosphingolipid.

このデータベースではスフィンゴ脂質をスフィンゴリン脂質とスフィンゴ糖脂質に分けています。

Sphingolipid Overview

Glycosphingolipid
LBSnn.png
スフィンゴ糖脂質

Phosphosphingolipid
(including GIPC)
LBSPP.png
スフィンゴリン脂質

Cerebroside (n = 1)
Glycosylceramide (n > 1)
Ceramide and long chain bases

History

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 スフィンゴ脂質

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) Code 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 (NeuAcα2-3)Galβ1-4Glcβ1-Cer
Structure.*\(?NeuAca2-8NeuAca2-3\)?Galb1-4Glcb1-Cer|b-series (NeuAcα2-8NeuAcα2-3)Galβ1-4Glcβ1-Cer
Structure.*\(?NeuAca2-8NeuAca2-8NeuAca2-3\)?Galb1-4Glcb1-Cer|c-series (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 Manα1-3Manβ1-4Glcb1.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(A∼R) 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, Damian, Smith, Cummings (1992) J Biol Chem 267(4):2251-2257 PMID 1733932

First (s1) Code for Phosphoosphingolipid

First sugar Code Root sequence Major Series
No Sugar Attached P1 (LBSP) R-P-Cer Sphingomyelin and Phosphoetanolamine-ceramide
(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) Code for subsequent sugars

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.

L

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