α,β-Difluoromethylene Deoxynucleoside 5′-Triphosphates: A Convenient Synthesis of Useful Probes for DNA Polymerase β Structure and Function

被引：39

作者：

Upton, Thomas G. ^{[1
]}

Kashemirov, Boris A. ^{[1
]}

McKenna, Charles E. ^{[1
]}

Goodman, Myron F. ^{[1
]}

Prakash, G. K. Surya ^{[1
]}

Kultyshev, Roman ^{[1
]}

Batra, Vinod K. ^{[2
]}

Shock, David D. ^{[2
]}

Pedersen, Lars C. ^{[2
]}

Beard, William A. ^{[2
]}

Wilson, Samuel H. ^{[2
]}

机构：

[1] Univ So Calif, Dept Biol & Chem, Los Angeles, CA 90089 USA

[2] NIEHS, Struct Biol Lab, NIH, Res Triangle Pk, NC 27709 USA

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 09期

关键词：

VIRUS-1; REVERSE-TRANSCRIPTASE; PHOSPHONATE ANALOGS; NUCLEOSIDE TRIPHOSPHATE; PERCHLORYL FLUORIDE; ATP ANALOGS; FIDELITY; ACID; NUCLEOTIDES; SPECIFICITY; DERIVATIVES;

D O I：

10.1021/ol701755k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

alpha,beta-Difluoromethylene deoxynucleoside 5'-triphosphates (dNTPs, N = A or C) are advantageously obtained via phosphorylation of corresponding dNDP analogues using catalytic ATP, PEP, nucleoside diphosphate kinase, and pyruvate kinase. DNA pol beta K-d values for the alpha,beta-CF2 and unmodified dNTPs, alpha,beta-NH dUTP, and the alpha,beta-CH2 analogues of dATP and dGTP are discussed in relation to the conformations of alpha,beta-CF2 dTTP versus alpha,beta-NH dUTP bound into the enzyme active site.

引用

页码：1883 / 1886

页数：4

共 43 条

[1] (DIFLUOROMETHYLENE)PHOSPHATES OF GUANINE NUCLEOSIDES AS PROBES OF DNA-POLYMERASES AND G-PROTEINS
ARABSHAHI, L
KHAN, NN
BUTLER, M
NOONAN, T
BROWN, NC
WRIGHT, GE
[J]. BIOCHEMISTRY, 1990, 29 (29) : 6820 - 6826
[2] BARRIE SE, 1984, ADV EXP MED BIOL, V165, P371
[3] Structures of DNA polymerase β with active-site mismatches suggest a transient abasic site intermediate during misincorporation
Batra, Vinod K.
Beard, William A.
Shock, David D.
Pedersen, Lars C.
Wilson, Samuel H.
[J]. MOLECULAR CELL, 2008, 30 (03) : 315 - 324
[4] Magnesium-induced assembly of a complete DNA polymerase catalytic complex
Batra, VK
Beard, WA
Shock, DD
Krahn, JM
Pedersen, LC
Wilson, SH
[J]. STRUCTURE, 2006, 14 (04) : 757 - 766
[5] Influence of DNA structure on DNA polymerase β active site function -: Extension of mutagenic DNA intermediates
Beard, WA
Shock, DD
Wilson, SH
[J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2004, 279 (30) : 31921 - 31929
[6] Structure and mechanism of DNA polymerase β
Beard, WA
Wilson, SH
[J]. CHEMICAL REVIEWS, 2006, 106 (02) : 361 - 382
[7] Loss of DNA polymerase β stacking interactions with templating purines, but not pyrimidines, alters catalytic efficiency and fidelity
Beard, WA
Shock, DD
Yang, XP
DeLauder, SF
Wilson, SH
[J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2002, 277 (10) : 8235 - 8242
[8] DNA structure and aspartate 276 influence nucleotide binding to human DNA polymerase β -: Implication for the identity of the rate-limiting conformational change
Berg, BJV
Beard, WA
Wilson, SH
[J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276 (05) : 3408 - 3416
[9] α-fluorinated phosphonates as substrate mimics for glucose 6-phosphate dehydrogenase:: the CHF stereochemistry matters
Berkowitz, DB
Bose, M
Pfannenstiel, TJ
Doukov, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (15) : 4498 - 4508
[10] MONOFLUORO-METHYLENEBISPHOSPHONIC AND DIFLUORO-METHYLENEBISPHOSPHONIC ACIDS - ISOPOLAR ANALOGS OF PYROPHOSPHORIC ACID
BLACKBURN, GM
ENGLAND, DA
KOLKMANN, F
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (17) : 930 - 932

← 1 2 3 4 5 →