Application of L-threonine aldolase-catalyzed reaction to the preparation of protected 3R,5R-dihydroxy-L-homoproline as a mimetic of idulonic acid.
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.
Miura
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T
Frontier Research Program, The Institute of Physical and Chemical Research, Saitama, Japan.
Kajimoto
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T
D012696:Glycine Hydroxymethyltransferase / Q000737:chemistry*; D006493:Heparin / Q000031:analogs & derivatives / Q000737:chemistry; D006497:Heparan Sulfate / Q000031:analogs & derivatives / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D018716:Molecular Mimicry; D011392:Proline / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D014574:Uronic Acids / Q000737:chemistry*
D012696:Glycine Hydroxymethyltransferase; D006493:Heparin; D006497:Heparan Sulfate; D007202:Indicators and Reagents; D011392:Proline; D014574:Uronic Acids; C440211:N-benzyloxycarbonyl-3-O-tert-butyldimethylsilyl-5-hydroxyhomoproline; C440212:idulonic acid