Preparation of S‐ and N‐Linked Glycosylated Amino Acid Building Blocks for Solid‐phase Glycopeptide Library Synthesis*

* In memory of Professor Jacques H. van Boom.

Abstract

A general route for the preparation of 1,2‐trans‐linked S‐glycosylated amino acid building blocks by a Lewis‐acid‐promoted condensation of peracetylated glycosyl donors and N ^α‐Fmoc‐Cys‐OH, in good overall yield, is described. In addition, a short and time‐efficient route was applied for the synthesis of N‐glycosylated amino acid building blocks in good overall yields by coupling unprotected glycosylamines and N ^α‐Fmoc‐Asp(OH)‐O ^t Bu using TBTU activation.

* In memory of Professor Jacques H. van Boom.

Keywords:

• Glycosylated amino acid
• S‐Glycosidic linkage
• N‐Glycosidic linkage
• Glycopeptide

Acknowledgment

We are grateful for the financial support for this study provided by DSTL Porton Down, UK.

Notes

* In memory of Professor Jacques H. van Boom.