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Synthesis of homorhamnojirimycins and related trihydroxypipecolic acid derivatives via divergent bicyclic amino lactone intermediates: Inhibition of naringinase (L-rhamnosidase) and dTDP-rhamnose biosynthesis

Abstract:

A series of homorhamnqjirimycins and related compounds are prepared from two epimeric [2.2.2] bicyclic amino lactones 6 and 7 via the 2-azidoheptono-l,5-lactone 8, itself derived from L-rhamnose. Aminolysis and deprotection of the bicyclic lactones provides an efficient route to trihydroxypipecolic acid amide analogues of S-epi-L-rhamndpyranose 12a-d and L-rhamnopyranose 14a-d. Some of the L-rhamnopyranose analogues display inhibitory activity against naringinase (L-rhamnosidase) and dTDP-rha...

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Publication status:
Published

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Publisher copy:
10.1039/a904064a

Authors


Shilvock, JP More by this author
Wheatley, JR More by this author
Watson, AA More by this author
Griffiths, RC More by this author
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Journal:
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
Issue:
19
Pages:
2735-2745
Publication date:
1999-10-07
DOI:
EISSN:
1364-5463
ISSN:
0300-922X
URN:
uuid:0f90612b-3c3c-4141-9690-33048a606a27
Source identifiers:
37121
Local pid:
pubs:37121
Language:
English

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