Glucosylgalactosyl hydroxylysine
IUPAC 名称
(2S)-2,6-diamino-5-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2R,3R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}hexanoic acid
描述
Glucosylgalactosyl hydroxylysine is a Glycoside of hydroxylysine. Hydroxylation of lysine is an important post-translational modification of collagen, (PMID 10928217) a reaction catalyzed by the enzyme Lysyl hydroxylase (EC 1.14.11.4) forming hydroxylysine in collagens and other proteins with collagen-like amino acid sequences, by the hydroxylation of lysine residues in X-lys-gly sequences.
The hydroxylysine residues formed in the lysyl hydroxylase reaction have 2 important functions: first, their hydroxy groups serve as sites of attachment for carbohydrate units, either the monosaccharide galactose or the disaccharide glucosylgalactose; and second, they are essential for the stability of the intermolecular collagen crosslinks. (OMIM 153454)
Hydroxylysine-deficient skin collagen is manifested in Ehlers-Danlos syndrome, type VIA, A heritable disorder of connective tissue (PMID 5016372) [HMDB]
异构
NCC(CC[C@H](N)C(O)=O)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O[C@H]1O[C@H](CO)[C@@H](O)C(O)[C@H]1O
InChI标识符
InChI=1S/C18H34N2O13/c19-3-6(1-2-7(20)16(28)29)30-18-15(13(26)11(24)9(5-22)32-18)33-17-14(27)12(25)10(23)8(4-21)31-17/h6-15,17-18,21-27H,1-5,19-20H2,(H,28,29)/t6?,7-,8+,9+,10+,11-,12?,13-,14+,15+,17+,18+/m0/s1
键
UTIRJVJBKWSIOX-SRMFCGEKSA-N