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Looking glass inhibitors: synthesis of a potent naringinase inhibitor L-DIM [1,4-dideoxy-1,4-imino-L-mannitol], the enantiomer of DIM [1,4-dideoxy-1,4-imino-D-mannitol] a potent alpha-D-mannosidase inhibitor

Abstract:

The synthesis of l-DIM [1,4-dideoxy-1,4-imino-l-mannitol] and of 1,4-imino-d-glycero-l-talo-heptitol from d-glycero-d-gulo-heptono-1,4-lactone depends on the use of pentan-3-one to form two five ring ketals as described by Burke, rather than the formation of one five ring and one six ring ketal formed with acetone. l-DIM, the enantiomer of the potent α-d-mannosidase inhibitor DIM [1,4-dideoxy-1,4-imino-d-mannitol] is a good inhibitor of naringinase (an α-l-rhamnosidase) with a K of 3.63 μM. 1...

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Publication status:
Published

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Journal:
TETRAHEDRON-ASYMMETRY
Volume:
18
Issue:
2
Pages:
282-289
Publication date:
2007-02-14
DOI:
EISSN:
1362-511X
ISSN:
0957-4166
Source identifiers:
40274
Pubs id:
pubs:40274
UUID:
uuid:b6cd25c8-cce6-4bf4-a7c1-936dbbb8dbaa
Local pid:
pubs:40274
Deposit date:
2012-12-19

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