N-Acetyl-D-Mannosamine → GlyTouCan:G94857MO

HRID 962419

Reaktionsgleichung

Reaktionsgleichung von HRID 962419
[C:1]([NH:4][C@H:5]1[C@@H:11]([OH:12])[C@H:10]([OH:13])[C@@H:9]([CH2:14][OH:15])[O:8][CH:6]1[OH:7])(=[O:3])[CH3:2].C([CH2:18][C:19]([O-])=[O:20])=C.C(OCC)(=O)C.CO>CN(C=O)C>[C:19]([O:15][CH2:14][C@H:9]1[O:8][CH:6]([OH:7])[C@@H:5]([NH:4][C:1](=[O:3])[CH3:2])[C@@H:11]([OH:12])[C@@H:10]1[OH:13])(=[O:20])[CH3:18]

Komponenten

5

Edukt 3

HCID 439281N-Acetyl-D-MannosamineHCID 69710893-Butenoic acid, ion(1-)HCID 21584119Ethylacetate methanol

Produkt 1

HCID 14160859GlyTouCan:G94857MOAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In 2 mL of DMF were suspended 500 mg (2.2 mmol) of N-acetylmannosamine. Vinylacetate (1 mL, 5 equivalent) and 160 mg of subtilisin mutant 8399 [Zhong et al., J. Am. Chem. Soc., 113:683 (1991)] were then added and the suspension was stirred vigorously at room temperature. The reaction progress was monitored by TLC with ethyl acetate/methanol (2/1). After 5 hours when the formation of the di-acetylated derivatives began, the reaction was stopped by evaporating the vinylacetate and DMF. Methanol was then added to dissolve the sugar. After the enzyme and salt were filtered off, the filtrate was concentrated. The residual syrup was chromatographed on a silica gel, with ethyl acetate/methanol (10/1) to give 6-O-Acetyl N-acetylmannosamine (92 percent) as α/β mixture (3:1) based on the NMR spectrum.

Aufarbeitung

  1. customby evaporating the vinylacetate and DMF
  2. additionMethanol was then added
  3. dissolutionto dissolve the sugar
  4. filtrationAfter the enzyme and salt were filtered off
  5. concentrationthe filtrate was concentrated
  6. customThe residual syrup was chromatographed on a silica gel, with ethyl acetate/methanol (10/1)

Quellen und Nachweise

ORD-Eintrag
ord-a1e01a17b76e4861aa30b7110edb48ad
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05759823

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