Modular Synthesis of Nucleoside Diphosphate Sugar Analogues Using Chlorosulfonyl Isocyanate and Dichlorophosphoryl Isocyanate

Organic Letters 2026

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Authors: Roy Steneker, Koen J. Rijpkema, Tim P. Ofman, Mert Sagiroglugil, Carme Rovira, Gijsbert A. van der Marel, Dmitri V. Filippov, Herman S. Overkleeft, Jeroen D. C. Codée
DOI: 10.1021/acs.orglett.5c04568
Cited by: 1
References: 35

Abstract

Pyrophosphates are central to biology, and synthetic pyrophosphate isosteres are widely sought to create biomimetic molecules to study diverse biochemical processes. We describe a flexible, modular synthesis of nucleoside diphosphate sugar analogues by linking carbasugars and nucleosides with the dual electrophilic reagents chlorosulfonyl isocyanate and dichlorophosphoryl isocyanate, introducing sulfonyl- and phosphoryl-carbamate linkages as pyrophosphate isosteres, respectively. The resulting GDP-fucose and UDP-GlcNAc analogues may inhibit glycosyltransferases and serve as tools for studying pyrophosphate-processing enzymes.

Fields of Study & Subjects

Carbohydrate Chemistry and Synthesis Click Chemistry and Applications HIV/AIDS drug development and treatment

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
3
Pages
912–916
Publication date
13 January 2026
Language
EN