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4-C-Me-DAB and 4-C-Me-LAB - enantiomeric alkyl-branched pyrrolidine iminosugars - are specific and potent α-glucosidase inhibitors; acetone as the sole protecting group.

Abstract:

The syntheses of 4-C-Me-DAB [1,4-dideoxy-1,4-imino-4-C-methyl-d-arabinitol] from l-erythronolactone and of 4-C-Me-LAB [from d-erythronolactone] require only a single acetonide protecting group. The effect of pH on the NMR spectra of 4-C-Me-DAB [pK(a) of the salt around 8.4] is discussed and illustrates the need for care in analysis of both coupling constants and chemical shift. 4-C-Me-DAB (for rat intestinal sucrase K(i) 0.89 μM, IC(50) 0.41 μM) is a competitive - whereas 4-C-Me-LAB (for rat ...

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Publication status:
Published

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Authors


da Cruz, FP More by this author
Newberry, S More by this author
Jenkinson, SF More by this author
More by this author
Institution:
University of Oxford
Department:
Oxford, MSD, Biochemistry
Butters, TD More by this author
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Journal:
Tetrahedron letters
Volume:
52
Issue:
2
Pages:
219-223
Publication date:
2011-01-05
DOI:
ISSN:
0040-4039
URN:
uuid:fc6c1ada-8408-4958-b541-08cdfc718624
Source identifiers:
107197
Local pid:
pubs:107197
Language:
English

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