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

HRID 363007

Reaktionsgleichung

Reaktionsgleichung von HRID 363007
[CH3:1][C:2]([NH:4][C@H:5]1[C@H:10]([C@H:11]([OH:16])[C@H:12]([OH:15])[CH2:13][OH:14])[O:9][C@:8]([O:20]P(OC[C@H]2O[C@@H](N3C(=O)N=C(N)C=C3)[C@H](O)[C@@H]2O)(O)=O)([C:17]([OH:19])=[O:18])[CH2:7][C@@H:6]1[OH:41])=[O:3].OC(C1(O[C@@H]([C@@H]([C@@H](CO)O)O)[C@H](NC(C)=O)[C@@H](O)C1)O)=O.CC(NC1C(C(O)C(O)CO)OC(OP(OC[C@H]2O[C@@H](N3C(=O)N=C(N)C=C3)[C@H](O)[C@@H]2O)([O-])=O)(C(O)=O)CC1O)=O.[Na+].[O:105]([C@H]1[C@H](O)[C@@H](CO)O[C@@H](O)[C@@H]1NC(C)=O)[C@@H:106]1[O:114][C@H:113]([CH2:115][OH:116])[C@H:111]([OH:112])[C@H:109](O)[C@H:107]1[OH:108].O([C@H]1[C@@H](O)[C@@H](CO)OC(O)[C@@H]1NC(C)=O)[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O.O=C[C@@H]([C@H]([C@H]([C@@H](CO)O)O)O)O>>[OH:19][C:17]([C@@:8]1([O:9][C@@H:10]([C@@H:11]([C@@H:12]([CH2:13][OH:14])[OH:15])[OH:16])[C@H:5]([NH:4][C:2]([CH3:1])=[O:3])[C@@H:6]([OH:41])[CH2:7]1)[O:20][C@H:109]1[C@@H:111]([OH:112])[C@@H:113]([CH2:115][OH:116])[O:114][C@@H:106]([OH:105])[C@@H:107]1[OH:108])=[O:18]

Komponenten

7

Edukt 6

HCID 439197N-Acetyl-Neuraminic AcidHCID 4412482-(acetylamino)-2-deoxy-3-O-beta-D-galactopyranosyl-D-galactopyranoseHCID 448209CMP-Neu5AcHCID 3037556(2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 10177989beta-D-Galp-(1->3)-beta-D-GlcpNAcHCID 16760374sodium;[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 phosphate

Produkt 1

HCID 52893663-O-(N-Acetyl-alpha-neuraminosyl)-beta-D-galactopyranose

Versuchsvorschrift

The resulting CMP-sialic acid analogue (which in FIG. 3 is illustrated as the CMP 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 or the βGal(1→3)GalNAc 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→3)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.

Quellen und Nachweise

ORD-Eintrag
ord-857116f0617b473b8f8deecd872b47d2
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05872096

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