Investigations into the decomposition of aminoacyl-substituted monosaccharide scaffolds from a drug discovery library

He, Q. Q., Wimmer, N., Verquin, G., Meutermans, W. and Ferro, V. (2015) Investigations into the decomposition of aminoacyl-substituted monosaccharide scaffolds from a drug discovery library. Organic and Biomolecular Chemistry, 13 13: 4070-4079. doi:10.1039/C5OB00122F


Author He, Q. Q.
Wimmer, N.
Verquin, G.
Meutermans, W.
Ferro, V.
Title Investigations into the decomposition of aminoacyl-substituted monosaccharide scaffolds from a drug discovery library
Journal name Organic and Biomolecular Chemistry   Check publisher's open access policy
ISSN 1477-0520
1477-0539
Publication date 2015-04
Year available 2015
Sub-type Article (original research)
DOI 10.1039/C5OB00122F
Open Access Status Not Open Access
Volume 13
Issue 13
Start page 4070
End page 4079
Total pages 10
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Collection year 2016
Language eng
Formatted abstract
This study investigated the unexpected decomposition and associated intermediates of compound 1, a specific member of a drug discovery library based on a monosaccharide scaffold. LC/MS and NMR spectroscopic analyses indicated that, under acidic conditions, 1 can be converted into the 4-aminogalactoside 2, due to cleavage of the 4-aminobutanoyl side chain. The reaction occurs most likely through an initial intramolecular amino–amide interaction, followed by an N- to O-acyl transfer of the side chain from C-4 to the C-6 position to form an ester intermediate (5), detectable by NMR, and subsequent hydrolysis. Similar decomposition reactions could be induced in selected compounds with similar structures, containing a free hydroxyl group at C-6 and a 4-aminobutanoyl side chain at C-4 of an aminogalactoside. Furthermore, three model compounds were synthesized without a C-6 hydroxyl group and with different length aminoalkanoyl side chains at the C-4 position. The model compounds all decomposed under acidic conditions, but at different rates and much slower when compared with compound 1, suggesting that both the C-6 hydroxyl group and the length of the side chain have an influence on stability.
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2016 Collection
School of Chemistry and Molecular Biosciences
 
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Created: Fri, 06 Mar 2015, 13:09:57 EST by Mrs Louise Nimwegen on behalf of School of Chemistry & Molecular Biosciences