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Issue 15, 2020
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Synthesis of orthogonally protected and functionalized bacillosamines

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Abstract

2,4-Diamino-2,4,6-trideoxyglucose (bacillosamine) is a monosaccharide found in many pathogenic bacteria, variation in the functionalities appended to the amino groups occurs depending on the species the sugar is derived from. We here report the first synthesis of bacillosamine synthons that allow for the incorporation of two different functionalities at the C-2-N-acetyl and C-4-amines. We have developed chemistry to assemble a set of conjugation ready Neisseria meningitidis C-2-N-acetyl bacillosamine saccharides, carrying either an acetyl or (R)- or (S)-glyceroyl at the C-4 amine. The glyceroyl bacillosamines have been further extended at the C-3-OH with an α-D-galactopyranose to provide structures that occur as post-translational modifications of N. meningitidis PilE proteins, which make up the bacterial pili.

Graphical abstract: Synthesis of orthogonally protected and functionalized bacillosamines

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Supplementary files

Article information


Submitted
05 Feb 2020
Accepted
25 Mar 2020
First published
25 Mar 2020

This article is Open Access

Org. Biomol. Chem., 2020,18, 2834-2837
Article type
Communication

Synthesis of orthogonally protected and functionalized bacillosamines

J. van Mechelen, J. Voorneveld, H. S. Overkleeft, D. V. Filippov, G. A. van der Marel and J. D. C. Codée, Org. Biomol. Chem., 2020, 18, 2834
DOI: 10.1039/D0OB00256A

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