Udp-Galactose → Uridine-Diphosphate-N-Acetylglucosamine

Beteiligte Stoffe

Reaktionsschritte

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.

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