Stereoselective synthesis of Neu5Acalpha(2-->5)Neu5Gc: the building block of oligo/poly(-->5-O(g)(lycolyl)Neu5Gcalpha2-->) chains in sea urchin egg cell surface glycoprotein.
The synthesis of a sialic acid dimer derivative, Neu5Acalpha(2-->5)Neu5Gc, is described. The synthetic strategy is based on the use of allyl alcohol to achieve an exclusive alpha-sialylation product. The allyloxy group is also a latent glycolic acid that provides the subsequent coupling with neuraminate with minimal protection-deprotection manipulations.
Fan
Gang-Ting
GT
Academia Sinica, Institute of Chemistry, Nankang, Taipei 115, Taiwan.
Lee
Chen-Chang
CC
Lin
Chun-Cheng
CC
Fang
Jim-Min
JM
D000818:Animals; D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000737:chemistry*; D005260:Female; D008562:Membrane Glycoproteins / Q000737:chemistry*; D008958:Models, Molecular; D019158:N-Acetylneuraminic Acid; D010063:Ovum / Q000737:chemistry*; D012617:Sea Urchins; D013237:Stereoisomerism
D004187:Disaccharides; D008562:Membrane Glycoproteins; D019158:N-Acetylneuraminic Acid