Journal of Organic Chemistry p. 3663 - 3670 (1995)
Update date:2022-08-06
Topics:
Fitz, Wolfgang
Schwark, Jan-Robert
Wong, Chi-Huey
The four stereoisomeric aldotetroses were accepted with different reactivities by N-acetylneuraminic acid aldolase.C(3)-modified D-mannose and D-glucose derivatives, respectively, failed to undergo enzymatic aldol addition.Based on the observed reactivities of the tested compounds (about 58), a mechanistic scheme is proposed which relates substrate structure, reactivity and stereochemical outcome observed in Neu5Ac aldolase-catalyzed reactions.The condensation products obtained in the L-erythrose and D-threose reactions are side-chain modified sialic acid and D-KDO derivatives, respectively, of biological interest.
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