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...

Mô tả đầy đủ

Chi tiết về thư mục
Những tác giả chính: Hakansson, A, van Ameijde, J, Guglielmini, L, Horne, G, Nash, R, Evinson, E, Kato, A, Fleet, G
Định dạng: Journal article
Được phát hành: 2007
Miêu tả
Tóm tắt: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.