71274-31-2Relevant academic research and scientific papers
Glycopeptide Synthesis: Selective C-terminal Deblocking and Peptide Chain Elongation of Glucosylserine Derivatives
Buchholz, Michael,Kunz, Horst
, p. 1859 - 1885 (2007/10/02)
Benzyloxycarbonyl-(Z-)serine 2-bromoethyl ester (3b) reacts with 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl bromide (14) to give the glucosylserine ester 15.After conversion into the corresponding 2-iodoethyl ester 23 the carboxylic group is deblocked selectively by reductive elimination using zinc.In this procedure the Z and the carbohydrate protective functions as well as the sensitive O-glycoside bond remain unaffected.The glycosylserine 24 is condensed with amino acid 2-bromoethyl esters 2 to form protected glycodipeptide 2-bromoethyl esters 18 which are extended to give glycotripeptide esters 25 after selective carboxyl deblocking.Whereas protected serine dipeptides 5 are glycosylated with 14 to form the conjugates 18, the glycosylation of the serine tripeptides 10 was not successful.
