Udp-Galactose → Uridine-Diphosphate-N-Acetylglucosamine

HRID 928872

Reaktionsgleichung

Reaktionsgleichung von HRID 928872
[OH:1][CH:2]1[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:3]1[NH2:12].[CH:13]1[C:19](=[O:20])[NH:18][C:16](=[O:17])[N:15]([C@@H:21]2[O:25][C@H:24]([CH2:26][O:27][P:28]([O:31][P:32]([OH:35])([OH:34])=[O:33])([OH:30])=[O:29])[C@@H:23]([OH:36])[C@H:22]2[OH:37])[CH:14]=1.OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O.OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O.[CH:62]1[C:68](=[O:69])[NH:67][C:65](=[O:66])[N:64]([C@@H:70]2[O:74][C@H:73]([CH2:75][O:76][P:77]([O:80][P:81]([O:84][C@H:85]3[O:90][C@H:89]([CH2:91][OH:92])[C@H:88]([OH:93])[C@H:87]([OH:94])[C@H:86]3O)([OH:83])=[O:82])([OH:79])=[O:78])[C@@H:72]([OH:96])[C@H:71]2[OH:97])[CH:63]=1>>[CH3:13][C:19]([NH:18][C@H:86]1[C@@H:85]([O:84][P:81]([O:80][P:77]([O:76][CH2:75][C@H:73]2[O:74][C@@H:70]([N:64]3[C:65](=[O:66])[NH:67][C:68](=[O:69])[CH:62]=[CH:63]3)[C@H:71]([OH:97])[C@@H:72]2[OH:96])([OH:79])=[O:78])([OH:83])=[O:82])[O:90][C@H:89]([CH2:91][OH:92])[C@@H:88]([OH:93])[C@@H:87]1[OH:94])=[O:20].[CH:13]1[C:19](=[O:20])[NH:18][C:16](=[O:17])[N:15]([C@@H:21]2[O:25][C@H:24]([CH2:26][O:27][P:28]([O:31][P:32]([OH:34])([OH:35])=[O:33])([OH:30])=[O:29])[C@@H:23]([OH:36])[C@H:22]2[OH:37])[CH:14]=1.[OH:1][CH:2]1[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@@H:3]1[NH2:12].[CH3:13][C:19]([NH:18][C@@H:86]1[C@@H:85]([O:84][P:81]([O:80][P:77]([O:76][CH2:75][C@H:73]2[O:74][C@@H:70]([N:64]3[C:65](=[O:66])[NH:67][C:68](=[O:69])[CH:62]=[CH:63]3)[C@H:71]([OH:97])[C@@H:72]2[OH:96])([OH:79])=[O:78])([OH:83])=[O:82])[O:90][C@H:89]([CH2:91][OH:92])[C@@H:88]([OH:93])[C@@H:87]1[OH:94])=[O:20]

Komponenten

7

Edukt 4

HCID 18068Udp-GalactoseHCID 18950D-MannoseHCID 439213D-GlucosamineHCID 131735082UDP Man

Produkt 3

HCID 445675Uridine-Diphosphate-N-AcetylglucosamineHCID 449043UDP-N-acetyl-alpha-D-mannosamineHCID 131735081UDP ManNH2

Versuchsvorschrift

The synthesis of all other UDP-sugars in Table 6 was carried out using the one-pot three-enzyme system shown in FIG. 9. As shown in Table 6, the one-pot three-enzyme system provided excellent yields for the formation of UDP-Gal (T6-16, 86%), UDP-ManF (T6-27, 92%), and UDP-ManN3 (T6-29, 90%) from the corresponding monosaccharides Gal (T6-1), ManF (T6-12), and ManN3 (T6-14), respectively. Three of the derivatives of UDP-Glc including UDP-2-deoxyGlc (T6-22), UDP-GlcNH2 (T6-23), and UDP-GlcN3 (T6-24) were obtained from 2-deoxyGlc (T6-7), glucosamine (GlcNH2, T6-8) and GlcN3 (T6-9) in 56%, 43%, and 61% yields, respectively. The moderate yields for these three compounds may be attributed by less optimal NahK kinase activity for GlcNH2 (T6-8) and GlcN3 (T6-9), and the less optimal BLUSP activity for 2-deoxyGlc (T6-7). UDP-Man (T6-26) was synthesized from Man (T6-11) in moderate 60% yield using the one-pot three-enzyme system and the moderate yield was most likely due to the less optimal activity of BLUSP towards Man-1-P. The synthesis of four UDP-Gal derivatives including its 2-deoxy, 2-deoxy-2-amido-, 2-deoxy-2-azido-, and 2-deoxy-2-acetamido-derivatives (T6-17-T6-20) using the one-pot three-enzyme system was not successful. In addition, UDP-GlcNAc (T6-25), UDP-ManNH2 (T6-28), and UDP-ManNAc (T6-30) could not be produced from the corresponding monosaccharides (T6-10, T6-13, and T6-15) using the one-pot three-enzyme system. These were most likely due to the substrate restriction of BLUSP instead of kinases used.

Aufarbeitung

  1. customT6-8) and GlcN3 (T6-9) in 56%, 43%, and 61% yields
  2. customThe moderate yields for these three compounds
  3. customthe moderate yield

Quellen und Nachweise

ORD-Eintrag
ord-e12bd31515194943a97a9c1214a631e5
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290530B2

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