131613-80-4Relevant articles and documents
Aldotetroses and C(3)-Modified Aldohexoses as Substrates for N-Acetylneuraminic Acid Aldolase: A Model for the Explanation of the Normal and the Inversed Stereoselectivity
Fitz, Wolfgang,Schwark, Jan-Robert,Wong, Chi-Huey
, p. 3663 - 3670 (2007/10/02)
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.