A complete change of stereoselectivity in sialic acid aldolase reactions: a novel synthetic route to the KDO type of nine-carbon L-sugars

1991 ◽  
Vol 113 (20) ◽  
pp. 7816-7818 ◽  
Author(s):  
Christine Gautheron-Le Narvor ◽  
Yoshitaka Ichikawa ◽  
Chi Huey Wong
Keyword(s):  
Sialic Acid ◽  
Synthetic Route ◽  
Sialic Acid Aldolase

Chemoenzymatic synthesis of ring 18O-labeled sialic acid

2008 ◽  
Vol 86 (11) ◽  
pp. 1005-1009 ◽  
Author(s):  
Deepani Indurugalla ◽  
Andrew J Bennet
Keyword(s):  
Sialic Acid ◽  
Functional Group ◽  
Chemoenzymatic Synthesis ◽  
Hydroxyl Group ◽  
Synthetic Route ◽  
Acetylneuraminic Acid ◽  
O 18 ◽  
Sialic Acid Aldolase

Methyl 4,6-O-benzylidene-α-D-glucopyranoside was converted into methyl 2-azido-2-deoxy-4,6-O-benzylidene-α-D-altropyranoside via a synthetic route that incorporated two inversions of configuration. Activation of the C-3 hydroxyl group as a triflate ester followed by an SN2 reaction with O-18 labeled benzoate gave, after standard functional group manipulations, 2-acetamido-2-deoxy-D-(3-18O)mannose. Coupling of the labeled N-acetyl-mannosamine with pyruvate was catalyzed by sialic acid aldolase to give ring-oxygen-labeled sialic acid in an overall yield of 11.4% over 10 steps.Key words: N-acetylneuraminic acid, sialic acid oxygen-18, chemoenzymatic.

scholarly journals Modulation of Substrate Specificities of d-Sialic Acid Aldolase through Single Mutations of Val-251

2011 ◽  
Vol 286 (16) ◽  
pp. 14057-14064 ◽  
Author(s):  
Chien-Yu Chou ◽  
Tzu-Ping Ko ◽  
Kuan-Jung Wu ◽  
Kai-Fa Huang ◽  
Chun-Hung Lin ◽  
...  
Keyword(s):  
Sialic Acid ◽  
Substrate Specificities ◽  
Sialic Acid Aldolase

Generation of a dynamic combinatorial library using sialic acid aldolase and in situ screening against wheat germ agglutinin

Tetrahedron ◽  
2004 ◽  
Vol 60 (3) ◽  
pp. 771-780 ◽  
Author(s):  
Roger J. Lins ◽  
Sabine L. Flitsch ◽  
Nicholas J. Turner ◽  
Ed Irving ◽  
Stuart A. Brown
Keyword(s):  
Sialic Acid ◽  
Wheat Germ Agglutinin ◽  
Wheat Germ ◽  
Combinatorial Library ◽  
Dynamic Combinatorial Library ◽  
Sialic Acid Aldolase

scholarly journals Pasteurella multocida sialic acid aldolase: a promising biocatalyst

2008 ◽  
Vol 79 (6) ◽  
Author(s):  
Yanhong Li ◽  
Hai Yu ◽  
Hongzhi Cao ◽  
Kam Lau ◽  
Saddam Muthana ◽  
...  
Keyword(s):  
Sialic Acid ◽  
Pasteurella Multocida ◽  
Sialic Acid Aldolase ◽  
Aldolase A
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