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Synthesis of the enantiomers of XYLNAc and LYXNAc: comparison of β-N-acetylhexosaminidase inhibition by the 8 stereoisomers of 2-N-acetylamino-1,2,4-trideoxy-1,4-iminopentitols.

Abstract:

The enantiomers of XYLNAc (2-N-acetylamino-1,2,4-trideoxy-1,4-iminoxylitol) are prepared from the enantiomers of glucuronolactone; the synthesis of the enantiomers of LYXNAc (2-N-acetylamino-1,2,4-trideoxy-1,4-iminolyxitol) from an L-arabinono-δ-lactone and a D-ribono-δ-lactone is reported. A comparison is made of the inhibition of β-N-acetylhexosaminidases (HexNAcases) and α-N-acetylgalactosaminidase (α-GalNAcase) by 8 stereoisomeric 2-N-acetylamino-1,2,4-trideoxy-1,4-iminopentitols; their N...

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Publication status:
Published

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Publisher copy:
10.1039/c4ob00097h

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Journal:
Organic and biomolecular chemistry
Volume:
12
Issue:
23
Pages:
3932-3943
Publication date:
2014-06-01
DOI:
EISSN:
1477-0539
ISSN:
1477-0520
Source identifiers:
465144
Language:
English
Keywords:
Pubs id:
pubs:465144
UUID:
uuid:cbbd340d-9f45-48c9-885e-668384ebe7ce
Local pid:
pubs:465144
Deposit date:
2014-07-05

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