Synthesis and characterization of 1-deoxy-. beta. -D-glucopyranosyl-methanephosphonyl-5'-uridine monophosphate: a phosphono analog of UDP-glucose
The phosphono analog of UDP-glucose (UDPG) has been synthesized as a first entry into potential dead-end inhibitors of glycosyltransferases using UDP-sugars such as UDP-glucuronyltransferase and possible alternative substrates for UDPG dehydrogenase and epimerase. 1-Deoxy-..beta..-D-glucopyranosylmethanephosphonate (G-1-CH/sub 2/P) was synthesized by modifications of literature procedures and characterized by /sup 1/H, /sup 31/P and /sup 13/C NMR. Condensation of G-1-CH/sub 2/P with UMP morpholidate gave the expected phosphono analog of UDPG (UDPCH/sub 2/G) in low yield. G-1-CH/sub 2/P was found to be a substrate for UTP: glucose-1-phosphate pyrophosphoyrlase. Thus, UDPCH/sub 2/G can be prepared enzymatically from G-1-CH/sub 2/P and UTP by the coupled action of the pyrophosphoyrlase and inorganic pyrophosphatase. Preliminary evidence suggests UDPCH/sub 2/G is a very poor substrate for UDPG dehydrogenase. Thus, efficient enzymatic synthesis of the phosphono analog (UDPCH/sub 2/GA) of UDP-glucuronate appears unlikely.
- Research Organization:
- Univ. of Maryland, College Park
- OSTI ID:
- 6173144
- Report Number(s):
- CONF-870644-
- Journal Information:
- Fed. Proc., Fed. Am. Soc. Exp. Biol.; (United States), Vol. 46:6; Conference: 78. annual meeting of the American Society of Biological Chemists conference, Philadelphia, PA, USA, 7 Jun 1987
- Country of Publication:
- United States
- Language:
- English
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550201* - Biochemistry- Tracer Techniques