Application of  L ‐threonine aldolase‐catalyzed reaction to the preparation of protected 3R,5R‐dihydroxy‐ L ‐homoproline as a mimetic of idulonic acid | Zendy

Miura Tsuyoshi | Zendy; Kajimoto Tetsuya | Zendy

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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.

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