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Literature DB >> 21462930

α-Azido bisphosphonates: synthesis and nucleotide analogues.

Brian T Chamberlain¹, Thomas G Upton, Boris A Kashemirov, Charles E McKenna.

Abstract

The first examples of α-azido bisphosphonates [(RO)(2)P(O)](2)CXN(3) (1, R = i-Pr, X = Me; 2, R = i-Pr, X = H; 3, R = H, X = Me; 4, R = H, X = H) and corresponding β,γ-CXN(3) dGTP (5-6) and α,β-CXN(3) dATP (7-8) analogues are described. The individual diastereomers of 7 (7a/b) were obtained by HPLC separation of the dADP synthetic precursor (14a/b).

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Year: 2011 PMID： 21462930 PMCID： PMC3112310 DOI： 10.1021/jo200045a

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

6 in total

1. (R)-beta,gamma-fluoromethylene-dGTP-DNA ternary complex with DNA polymerase beta.

Authors: Charles E McKenna; Boris A Kashemirov; Thomas G Upton; Vinod K Batra; Myron F Goodman; Lars C Pedersen; William A Beard; Samuel H Wilson
Journal: J Am Chem Soc Date: 2007-11-22 Impact factor: 15.419

2. Generation of iminyl copper species from alpha-azido carbonyl compounds and their catalytic C-C bond cleavage under an oxygen atmosphere.

Authors: Shunsuke Chiba; Line Zhang; Gim Yean Ang; Benjamin Wei-Qiang Hui
Journal: Org Lett Date: 2010-05-07 Impact factor: 6.005

3. Halogenated beta,gamma-methylene- and ethylidene-dGTP-DNA ternary complexes with DNA polymerase beta: structural evidence for stereospecific binding of the fluoromethylene analogues.

Authors: Vinod K Batra; Lars C Pedersen; William A Beard; Samuel H Wilson; Boris A Kashemirov; Thomas G Upton; Myron F Goodman; Charles E McKenna
Journal: J Am Chem Soc Date: 2010-06-09 Impact factor: 15.419

4. Alpha,beta-difluoromethylene deoxynucleoside 5'-triphosphates: a convenient synthesis of useful probes for DNA polymerase beta structure and function.

Authors: Thomas G Upton; Boris A Kashemirov; Charles E McKenna; Myron F Goodman; G K Surya Prakash; Roman Kultyshev; Vinod K Batra; David D Shock; Lars C Pedersen; William A Beard; Samuel H Wilson
Journal: Org Lett Date: 2009-05-07 Impact factor: 6.005

5. DNA polymerase beta fidelity: halomethylene-modified leaving groups in pre-steady-state kinetic analysis reveal differences at the chemical transition state.

Authors: Christopher A Sucato; Thomas G Upton; Boris A Kashemirov; Jorge Osuna; Keriann Oertell; William A Beard; Samuel H Wilson; Jan Florián; Arieh Warshel; Charles E McKenna; Myron F Goodman
Journal: Biochemistry Date: 2007-12-28 Impact factor: 3.162

6. A direct preparation of N-unsubstituted pyrrole-2,5-dicarboxylates from 2-azidocarboxylic esters.

Authors: Dariusz Ciez
Journal: Org Lett Date: 2009-10-01 Impact factor: 6.005

6 in total

7 in total

1. Stereospecific formation of a ternary complex of (S)-α,β-fluoromethylene-dATP with DNA pol β.

Authors: Brian T Chamberlain; Vinod K Batra; William A Beard; Anastasia P Kadina; David D Shock; Boris A Kashemirov; Charles E McKenna; Myron F Goodman; Samuel H Wilson
Journal: Chembiochem Date: 2012-02-07 Impact factor: 3.164

2. Remarkably Stereospecific Utilization of ATP α,β-Halomethylene Analogues by Protein Kinases.

Authors: Feng Ni; Alvin Kung; Yankun Duan; Vivek Shah; Carolina D Amador; Ming Guo; Xuegong Fan; Lin Chen; Yongheng Chen; Charles E McKenna; Chao Zhang
Journal: J Am Chem Soc Date: 2017-06-02 Impact factor: 15.419

3. β,γ-CHF- and β,γ-CHCl-dGTP diastereomers: synthesis, discrete 31P NMR signatures, and absolute configurations of new stereochemical probes for DNA polymerases.

Authors: Yue Wu; Valeria M Zakharova; Boris A Kashemirov; Myron F Goodman; Vinod K Batra; Samuel H Wilson; Charles E McKenna
Journal: J Am Chem Soc Date: 2012-05-18 Impact factor: 15.419