Reaktion #1016054

ord-e12bd31515194943a97a9c1214a631e5

Reaktionsgleichung

N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
GlcNH2
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP-Gal
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1.OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O
UDP Man
OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O
Man
→
CC(=O)N[C@H]1[C@@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O
UDP-GlcNAc
N[C@@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O.O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP ManNH2
CC(=O)N[C@@H]1[C@@H](OP(=O)(O)OP(=O)(O)OC[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O)[C@@H]1O
UDP-ManNAc

Edukte

N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
GlcNH2
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](CO)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H]2O)c(=O)[nH]1
UDP-Gal
O=c1ccn([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)O)[C@@H](O)[C@H]2O)c(=O)[nH]1.OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O
UDP Man
OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O
Man

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeT6-8) and GlcN3 (T6-9) in 56%, 43%, and 61% yields
  2. 2
    SonstigeThe moderate yields for these three compounds
  3. 3
    Sonstigethe moderate yield

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09290530B2uspto-grants-2016_03