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ChemMedChem. 2013 Apr;8(4):658-66. doi: 10.1002/cmdc.201200541. Epub 2013 Mar 6.

3-Hydroxyazetidine carboxylic acids: non-proteinogenic amino acids for medicinal chemists.

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  • 1Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA, UK.

Abstract

The formation from D-glucose of both enantiomers of 2,4-dideoxy-2,4-iminoribonic acid is the first chemical synthesis of unprotected 3-hydroxyazetidine carboxylic acids. The long-term stability of 3-hydroxyazetidine amides is established at acidic and neutral pH and implies their value as non-proteinogenic amino acid components of peptides, providing medicinal chemists with a new class of peptide isosteres. The structure of N,3-O-dibenzyl-2,4-dideoxy-2,4-imino-D-ribonic acid was established by X-ray crystallographic analysis. An N-methylazetidine amide derivative is a specific inhibitor of β-hexosaminidases at the micromolar level, and is only the second example of potent inhibition of any glycosidase by an amide of a sugar amino acid related to an iminosugar.

Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

PMID:
23468173
[PubMed - indexed for MEDLINE]
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