Synthesis of glycosylated 5-hydroxylysine, an important amino acid present in collagen-like proteins such as adiponectin.
The synthesis of naturally occurring glycosylated (2S,5R)-hydroxylysine still remains a challenge. This perspective highlights the importance of this post-translationally modified amino acid residue in the observed bioactivity of collagen and related collagen-like proteins such as adiponectin, an important target for the treatment of type II diabetes. Strategies employed to date for the syntheses of (2S,5R)-hydroxylysine and the methods to effect glycosylation of this modified amino acid are also summarized herein.
School of Chemical Sciences, The University of Auckland, 23 Symonds St, Auckland, 1142, New Zealand.
Katherine R
KR
Herbert
Geoffrey M
GM
Williams
Garth J S
GJ
Cooper
Margaret A
MA
Brimble
D052242:Adiponectin / Q000737:chemistry*; D006031:Glycosylation; D006901:Hydroxylysine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D052242:Adiponectin; D006901:Hydroxylysine