ChemInform Abstract: A Complete Change of Stereoselectivity in Sialic Acid Aldolase Reactions: A Novel Synthetic Route to the KDO Type of Nine-Carbon L Sugars.

ChemInform ◽  
2010 ◽  
Vol 23 (1) ◽  
pp. no-no
Author(s):  
C. GAUTHERON-LE NARVOR ◽  
Y. ICHIKAWA ◽  
C.-H. WONG
2008 ◽  
Vol 86 (11) ◽  
pp. 1005-1009 ◽  
Author(s):  
Deepani Indurugalla ◽  
Andrew J Bennet

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.


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

Tetrahedron ◽  
2004 ◽  
Vol 60 (3) ◽  
pp. 771-780 ◽  
Author(s):  
Roger J. Lins ◽  
Sabine L. Flitsch ◽  
Nicholas J. Turner ◽  
Ed Irving ◽  
Stuart A. Brown

Author(s):  
Yanhong Li ◽  
Hai Yu ◽  
Hongzhi Cao ◽  
Kam Lau ◽  
Saddam Muthana ◽  
...  

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