Premium
Application of L ‐threonine aldolase‐catalyzed reaction to the preparation of protected 3R,5R‐dihydroxy‐ L ‐homoproline as a mimetic of idulonic acid
Author(s) -
Miura Tsuyoshi,
Kajimoto Tetsuya
Publication year - 2001
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.1180
Subject(s) - chemistry , aldolase a , aldol condensation , aldol reaction , threonine , catalysis , stereochemistry , enzyme , chirality (physics) , fructose , biochemistry , serine , chiral symmetry breaking , physics , quantum mechanics , nambu–jona lasinio model , quark
A facile synthesis of 3R,5R‐dihydroxy‐ L ‐homoproline as idulonic acid mimic, of which the carboxyl and 3‐hydroxyl groups were protected, was attained using L ‐threonine aldolase‐catalyzed reaction. Idulonic acid is a key acidic sugar of the b‐FGF binding domain in heparin and heparan sulfate. Moreover, the synthetic precursor of N ‐acetyl‐4‐deoxy‐ D ‐mannosamine, which is a potent inhibitor of NeuAc synthase, was prepared from the side product of the enzymatic aldol condensation. Chirality 13:577–580, 2001. © 2001 Wiley‐Liss, Inc.