Synthesis of glycosylated 5-hydroxylysine, an important amino acid present in collagen-like proteins such as adiponectin

• Published in: Organic & biomolecular chemistry Vol. 10; no. 6; p. 1137
• Main Authors: Herbert, Katherine R, Williams, Geoffrey M, Cooper, Garth J S, Brimble, Margaret A
• Format: Journal Article
• Language: English
• Published: England 14-02-2012
• Subjects: Adiponectin - chemistry; Glycosylation; Hydroxylysine - analogs & derivatives; Hydroxylysine - chemical synthesis; Hydroxylysine - chemistry; Molecular Conformation; Stereoisomerism
• ISSN: 1477-0539
• DOI: 10.1039/c1ob06394d

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.