Synthesis of Glycopeptides with Lewisa Antigen Side Chain and HIV Peptide T Sequence Using the Trichloroethoxycarbonyl/Allyl Ester Protecting Group Combination

Horst Kunz; Joachim März

doi:10.1055/s-1992-21427

Synlett 1992; 1992(7): 591-593
DOI: 10.1055/s-1992-21427

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Synthesis of Glycopeptides with Lewis^a Antigen Side Chain and HIV Peptide T Sequence Using the Trichloroethoxycarbonyl/Allyl Ester Protecting Group Combination

Horst Kunz^* , Joachim März

^*Institut für Organische Chemie, Johannes Gutenberg-Universität Mainz, J.J.-Becher-Weg 18-20, D-6500 Mainz, Germany

Abstract

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The N-glycosidic conjugate of the Lewis^a antigen trisaccharide and an octapeptide sequence (peptide T) of gp 120 of HIV was synthesized using the 2,2,2-trichloroethoxycarbonyl (Teoc) group in combination with the allyl ester as the carboxy protection. These orthogonally stable protecting groups are selectively and alternatively removable under mild conditions without cleavage or anomerization of the glycosidic bonds.

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