Chemical models and their mechanistic implications for the transformation of 6-cyanouridine 5 '-monophosphate catalyzed by orotidine 5 '-monophosphate decarboxylase

• Published in: Chemical communications (Cambridge, England) Vol. 46; no. 26; pp. 4821 - 4823
• Main Authors: Wu, Yuen-Jen, Liao, Chen-Chieh, Jen, Cheng-Hung, Shih, Yu-Chiao, Chien, Tun-Cheng
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 14.07.2010
• Subjects: Barbiturates - chemistry; Biocatalysis; Catalytic Domain; Chemistry; Chemistry, Multidisciplinary; Models, Chemical; Orotidine-5'-Phosphate Decarboxylase - chemistry; Orotidine-5'-Phosphate Decarboxylase - metabolism; Physical Sciences; Science & Technology; Uridine Monophosphate - analogs & derivatives; Uridine Monophosphate - biosynthesis; Uridine Monophosphate - chemistry; Uridine Monophosphate - metabolism; PYRIMIDINE-DERIVATIVES; 6-CYANO-1,3-DIMETHYLURACIL; OMP DECARBOXYLASE; PROFICIENT ENZYME; OROTIDINE-5'-MONOPHOSPHATE DECARBOXYLASE; 5'-PHOSPHATE DECARBOXYLASE; 1,3-DIMETHYLOROTIC ACID; INTERMEDIATE; CRYSTALLOGRAPHY; MONOPHOSPHATE DECARBOXYLASE
• ISSN: 1359-7345; 1364-548X
• DOI: 10.1039/c001865a

The reactions of 6-cyano-1,3-dimethyluracil have been studied as chemical models to illustrate the mechanism for the transformation of 6-cyanouridine 5'-monophosphate (6-CN-UMP) to barbiturate ribonucleoside 5'-monophosphate (BMP) catalyzed by orotidine 5'-monophosphate decarboxylase (ODCase). The results suggest that the Asp residue in the ODCase active site plays the role of a general base in the transformation.