Synthesis of the protected glycotetrapeptide corresponding to the N-terminal amino acid sequence of [Thr3-0-α-D-galactopyranosyl]-vespulakinin 1

Add time:07/24/2019    Source:sciencedirect.com

The synthesis of the protected glycopeptide Z-Thr(tBu)-Ala-Thr-[α-D-Gal(Bzl)4 ]-Thr(tBu)-NHNH-Boc was performed in solution by a stepwise coupling strategy. Fmoc-Thr[(α+β)-D- Gal(Bzl)4]-0Su, obtained from the reducing sugar and the protected amino acid by the trifluoromethanesulfonic anhydride procedure, was reacted with H-Thr(tBu)-NHNH-Boc. The two diastereoisomers of the resulting glycosylated dipeptide derivative were purified and separated by column chromatography. The anomeric configuration of the 0-glycosidic linkage was assigned by 1H-NMR-spectroscopy. The α-anomeric glycodipeptide, obtained in a larger amount, was selectively deblocked at the amino function and acylated with Z-Thr(tBu)-Ala-OH in the presence of either IIDQ or EEDQ, to afford the desired protected glycotetrapeptide.

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