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

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 form...

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Bibliographic Details
Main Authors: Hakansson, A, van Ameijde, J, Guglielmini, L, Horne, G, Nash, R, Evinson, E, Kato, A, Fleet, G
Format: Journal article
Published: 2007
Description
Summary: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. 1,4-Imino-d-glycero-l-talo-heptitol is a moderate inhibitor of naringinase. © 2007 Elsevier Ltd. All rights reserved.