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Synthesis of S-glycosyl amino acids and S-glycopeptides via photoinduced click thiol–ene coupling

✍ Scribed by Michele Fiore; Mauro Lo Conte; Salvatore Pacifico; Alberto Marra; Alessandro Dondoni

Book ID
104098651
Publisher
Elsevier Science
Year
2011
Tongue
French
Weight
720 KB
Volume
52
Category
Article
ISSN
0040-4039

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✦ Synopsis

We report on the photoinduced addition of glycosyl thiols to alkenyl glycines (thiol-ene coupling) to give S-glycosyl amino acids in high yields (53-90%). One of the amino acids thus prepared was used in the construction of a tripeptide via solution phase chemistry. Moreover, a one-pot two-step approach to an S-glycopeptide was developed using glutathione (GSH) as model starting material. This approach involved GSH S-alkenylation followed by photoinduced hydrothiolation by a glycosyl thiol.

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