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Looking glass inhibitors: both enantiomeric N-benzyl derivatives of 1,4-dideoxy-1,4-imino-D-lyxitol [a potent competitive inhibitor of alpha-D-galactosidase] and of 1,4-dideoxy-1,4-imino-L-lyxitol [a weak competitive inhibitor of alpha-D-galactosidase] inhibit naringinase, an alpha-L-rhamnosidase competitively

Abstract:
Benzhydryl protection by diphenyldiazomethane of an alcohol in enantiomeric base-sensitive ribonolactones allows short efficient syntheses of 1,4-dideoxy-1,4-imino-d-lyxitol (DIL) and of 1,4-dideoxy-1,4-imino-l-lyxitol (LIL). DIL showed potent [Ki = 0.13 μM]-and LIL showed weak [Ki = 113 μM]-competitive inhibition of α-d-galactosidase. Both enantiomers N-benzyl-DIL [Ki = 64 μM] and N-benzyl-LIL [Ki = 13 μM] were moderate competitive inhibitors of naringinase, an α-l-rhamnosidase. © 2009 Elsevier Ltd. All rights reserved.
Publication status:
Published

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Journal:
TETRAHEDRON-ASYMMETRY
Volume:
20
Issue:
20
Pages:
2368-2373
Publication date:
2009-10-20
DOI:
EISSN:
1362-511X
ISSN:
0957-4166
URN:
uuid:ef34d8c3-ec94-4989-bb99-2f4354ecbe61
Source identifiers:
41489
Local pid:
pubs:41489
Language:
English

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