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Enantiospecific Synthesis of 1‐Azafagomine
Author(s) -
Ernholt Bettina V.,
Thomsen Ib B.,
Lohse Anders,
Plesner Igor W.,
Jensen Kenneth B.,
Hazell Rita G.,
Liang Xifu,
Jakobsen Astrid,
Bols Mikael
Publication year - 2000
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/(sici)1521-3765(20000117)6:2<278::aid-chem278>3.0.co;2-6
Subject(s) - xylose , reductive amination , chemistry , stereochemistry , glycoside hydrolase , enantiomer , yield (engineering) , enzyme , acetylation , enantioselective synthesis , amination , organic chemistry , biochemistry , catalysis , fermentation , materials science , metallurgy , gene
The two enantiomeric forms of the glycosidase inhibitor 1‐azafagomine have been synthesised starting from D ‐ and L ‐xylose for the first time (see picture). (−)‐1‐Azafagomine is a potent competitive glycosidase inhibitor, while (+)‐1‐azafagomine has no biological activity. Kinetic studies of the inhibition of a glucosidase by (−)‐1‐azafagomine revealed that the binding step of inhibitor to enzyme was slow, with no subsequent conformational rearrangement.