Literature DB >> 23935222

Improved synthesis of N1-substituted orotic acid derivatives.

Nicholas A Senger1, Jeannette T Bowler, Rene S Mercado, Sidney Lin, Weiming Wu.   

Abstract

An improved method for the synthesis of N1-substituted orotic acid derivatives is reported. The method involves sequential incorporation of nitrogen atoms to the pyrimidine structure from simple starting materials and thus allows the synthesis of N1-substituted orotic acid derivatives with single 15N label at either N-1 or N-3.

Entities:  

Keywords:  1-substituted orotic acid; 1-substituted uracil; 5-bromouracil; Orotic acid; dihydrouracil; orotidine

Year:  2013        PMID： 23935222      PMCID： PMC3735222          DOI： 10.1016/j.tetlet.2013.05.136

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  12 in total

1.  The mechanism of orotidine 5'-monophosphate decarboxylase: catalysis by destabilization of the substrate.

Authors:  W Y Feng; T J Austin; F Chew; S Gronert; W Wu
Journal:  Biochemistry       Date:  2000-02-22       Impact factor: 3.162

2.  Stability of the 6-carbanion of uracil analogues: mechanistic implications for model reactions of orotidine-5'-monophosphate decarboxylase.

Authors:  Freeman M Wong; Christina C Capule; Weiming Wu
Journal:  Org Lett       Date:  2006-12-21       Impact factor: 6.005

3.  Accelerated decarboxylation of 1,3-dimethylorotic acid in ionic liquid.

Authors:  Freeman M Wong; Weiming Wu
Journal:  Bioorg Chem       Date:  2006-02-24       Impact factor: 5.275

4.  A proficient enzyme revisited: the predicted mechanism for orotidine monophosphate decarboxylase.

Authors:  J K Lee; K N Houk
Journal:  Science       Date:  1997-05-09       Impact factor: 47.728

5.  [Synthesis of 1-cyclohexyl derivatives of nucleic acid pyrimidine bases and their analogs (electronic properties of N-heteroaromatics. XXV)].

Authors:  T Okano; S Goya; T Takahashi
Journal:  Yakugaku Zasshi       Date:  1968-09       Impact factor: 0.302

6.  Carbanions from decarboxylation of orotate analogs: stability and mechanistic implications.

Authors:  Fong Ying Yeoh; Roxanne R Cuasito; Christina C Capule; Freeman M Wong; Weiming Wu
Journal:  Bioorg Chem       Date:  2007-04-02       Impact factor: 5.275

7.  Stabilities of Uracil and Pyridone-Based Carbanions: A Systematic Study in the Gas Phase and Solution and Implications for the Mechanism of Orotidine-5'-Monophosphate Decarboxylase.

Authors:  Nicholas A Senger; Carly E Bliss; James R Keeffe; Scott Gronert; Weiming Wu
Journal:  Tetrahedron       Date:  2013-07-01       Impact factor: 2.457

8.  Rhodium(II)-catalyzed cyclization of amido diazo carbonyl compounds.

Authors:  A Padwa; T Hasegawa; B Liu; Z Zhang
Journal:  J Org Chem       Date:  2000-10-20       Impact factor: 4.354

9.  Surprisingly low aqueous acidity at the alpha-positions of pyridiniums and pyrimidinium: the role of solvation.

Authors:  Freeman M Wong; Christina C Capule; David X Chen; Scott Gronert; Weiming Wu
Journal:  Org Lett       Date:  2008-06-07       Impact factor: 6.005

10.  Orotic acid decarboxylation in water and nonpolar solvents: a potential role for desolvation in the action of OMP decarboxylase.

Authors:  Charles A Lewis; Richard Wolfenden
Journal:  Biochemistry       Date:  2009-09-15       Impact factor: 3.162
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  1 in total

1.  Convenient synthesis of N1-substituted orotic acid derivatives.

Authors:  Jeannette T Bowler; Caitlin R Clausen; Daniel J Blackburn; Weiming Wu
Journal:  Tetrahedron Lett       Date:  2014-11-19       Impact factor: 2.415
  1 in total

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