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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 962390Generated: October 25, 2026

N-Acetyl-Neuraminic Acid → 3-O-(N-Acetyl-alpha-neuraminosyl)-beta-D-galactopyranose

https://huagongshe.com/reaction/962390

Reaction equation

Participants

RoleNameHCIDCharge
ReactantN-Acetyl-Neuraminic AcidHCID 439197—
ReactantCMP-Neu5AcHCID 448209—
Reactant(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 3037556—
Reactantsodium;[5-acetamido-2-carboxy-4-hydroxy-6-(1,2,3-trihydroxypropyl)oxan-2-yl] [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphateHCID 16760374—
Product3-O-(N-Acetyl-alpha-neuraminosyl)-beta-D-galactopyranoseHCID 5289366—

Reaction Steps

The resulting CMP-sialic acid analogue (which in FIG. 3 is illustrated as the CKP derivative of Neu5Ac, i.e., CMP-Neu5Ac) is then combined with the derivatized βGal(1→3)βGlcNAc--OR compound in the presence of the βGal(1→3/4)βGlcNAc α(2→3)sialyltransferase under conditions wherein sialic acid is transferred to the 3 position of the galactose to form a αNeu5Ac(2→3)βGal linkage. Suitable conditions, known in the art, include the addition of the sialyltransferase to a mixture of the derivatized βGal(1→4)βGlcNAc--OR compound and of the CMP-sialic acid in a appropriate buffer such as 0.1M sodium cacodylate in appropriate conditions of pH and temperature such as at a pH of 6.5 to 7.5 and a temperature between 25° and 45° C., preferably 35°-40° C., while incubating for 12 hours to 4 days. The resulting sialylated product can be isolated and purified using conventional methodology comprising HPLC, ion exchange-, gel-, reverse-phase- or adsorption chromatography.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05759993
Source datasetuspto-grants-1998_06
ORD IDord-aa92e5b634af442cb38cd33dc66f1829
Source noteuspto-grants-1998_06