Literature DB >> 16497015

Synthesis and characterization of the oxidized dGTP lesions spiroiminodihydantoin-2'-deoxynucleoside-5'- triphosphate and guanidinohydantoin-2'-deoxynucleoside-5'- triphosphate.

Yu Ye1, James G Muller, Cynthia J Burrows.   

Abstract

Two convenient synthetic routes to the oxidized guanosine triphosphate lesions spiroiminodihydantoin-2'-deoxynucleoside-5'-triphosphate (dSpTP) and guanidinohydantoin-2'-deoxynucleoside-5'-triphosphate (dGhTP) are reported. Both two-electron oxidation of 2'-deoxy-7,8-dihydro-8-oxoguanosine-5'-triphosphate (dOGTP) using SO4*- generated photolytically from K2S2O8 or four-electron oxidation of 2'-deoxyguanosine-5'-triphosphate (dGTP) from singlet oxygen provide either dSpTP or dGhTP at pH 8.0 or 4.4, respectively. Highly purified triphosphates are obtained by ion pair reversed-phase HPLC.

Entities:  

Mesh：

Substances：

Year:  2006        PMID： 16497015      PMCID： PMC2442819          DOI： 10.1021/jo052484t

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


  34 in total

1.  Characterization of the dehydro-guanidinohydantoin oxidation product of guanine in a dinucleotide.

Authors:  Arkadiusz Chworos; Christel Seguy; Geneviève Pratviel; Bernard Meunier
Journal:  Chem Res Toxicol       Date:  2002-12       Impact factor: 3.739

2.  Incorporation of the guanosine triphosphate analogs 8-oxo-dGTP and 8-NH2-dGTP by reverse transcriptases and mammalian DNA polymerases.

Authors:  A S Kamath-Loeb; A Hizi; H Kasai; L A Loeb
Journal:  J Biol Chem       Date:  1997-02-28       Impact factor: 5.157

3.  Spiroiminodihydantoin is a major product in the photooxidation of 2'-deoxyguanosine by the triplet states and oxyl radicals generated from hydroxyacetophenone photolysis and dioxetane thermolysis.

Authors:  Waldemar Adam; Markus A Arnold; Matthias Grüne; Werner M Nau; Uwe Pischel; Chantu R Saha-Möller
Journal:  Org Lett       Date:  2002-02-21       Impact factor: 6.005

4.  A thymidine triphosphate shape analog lacking Watson-Crick pairing ability is replicated with high sequence selectivity.

Authors:  S Moran; R X Ren; E T Kool
Journal:  Proc Natl Acad Sci U S A       Date:  1997-09-30       Impact factor: 11.205

5.  Characterization of spiroiminodihydantoin as a product of one-electron oxidation of 8-Oxo-7,8-dihydroguanosine.

Authors:  W Luo; J G Muller; E M Rachlin; C J Burrows
Journal:  Org Lett       Date:  2000-03-09       Impact factor: 6.005

6.  Assessing the metabolic function of the MutT 8-oxodeoxyguanosine triphosphatase in Escherichia coli by nucleotide pool analysis.

Authors:  Mary Lynn Tassotto; Christopher K Mathews
Journal:  J Biol Chem       Date:  2002-02-20       Impact factor: 5.157

7.  Hydantoin derivative formation from oxidation of 7,8-dihydro-8-oxo-2'-deoxyguanosine (8-oxodG) and incorporation of 14C-labeled 8-oxodG into the DNA of human breast cancer cells.

Authors:  Sang Soo Hah; Hyung M Kim; Rhoda A Sumbad; Paul T Henderson
Journal:  Bioorg Med Chem Lett       Date:  2005-08-01       Impact factor: 2.823

8.  Spermine participates in oxidative damage of guanosine and 8-oxoguanosine leading to deoxyribosylurea formation.

Authors:  Mandy E Hosford; James G Muller; Cynthia J Burrows
Journal:  J Am Chem Soc       Date:  2004-08-11       Impact factor: 15.419

9.  Structure of human MTH1, a Nudix family hydrolase that selectively degrades oxidized purine nucleoside triphosphates.

Authors:  Masaki Mishima; Yasunari Sakai; Noriyuki Itoh; Hiroyuki Kamiya; Masato Furuichi; Masayuki Takahashi; Yuriko Yamagata; Shigenori Iwai; Yusaku Nakabeppu; Masahiro Shirakawa
Journal:  J Biol Chem       Date:  2004-05-07       Impact factor: 5.157

10.  Formation of 13C-, 15N-, and 18O-labeled guanidinohydantoin from guanosine oxidation with singlet oxygen. Implications for structure and mechanism.

Authors:  Yu Ye; James G Muller; Wenchen Luo; Charles L Mayne; Anthony J Shallop; Roger A Jones; Cynthia J Burrows
Journal:  J Am Chem Soc       Date:  2003-11-19       Impact factor: 15.419
View more
  5 in total

1.  Endonuclease and Exonuclease Activities on Oligodeoxynucleotides Containing Spiroiminodihydantoin Depend on the Sequence Context and the Lesion Stereochemistry.

Authors:  Xin Chen; Aaron M Fleming; James G Muller; Cynthia J Burrows
Journal:  New J Chem       Date:  2013-11-01       Impact factor: 3.591

Review 2.  Formation and processing of DNA damage substrates for the hNEIL enzymes.

Authors:  Aaron M Fleming; Cynthia J Burrows
Journal:  Free Radic Biol Med       Date:  2016-11-20       Impact factor: 7.376

3.  Klenow Fragment Discriminates against the Incorporation of the Hyperoxidized dGTP Lesion Spiroiminodihydantoin into DNA.

Authors:  Ji Huang; Craig J Yennie; Sarah Delaney
Journal:  Chem Res Toxicol       Date:  2015-11-24       Impact factor: 3.739

4.  Crystal structure of a replicative DNA polymerase bound to the oxidized guanine lesion guanidinohydantoin.

Authors:  Pierre Aller; Yu Ye; Susan S Wallace; Cynthia J Burrows; Sylvie Doublié
Journal:  Biochemistry       Date:  2010-03-23       Impact factor: 3.162

5.  Experimental and theoretical rationalization for the base pairing abilities of inosine, guanosine, adenosine, and their corresponding 8-oxo-7,8-dihydropurine, and 8-bromopurine analogues within A-form duplexes of RNA.

Authors:  Austin Skinner; Chou-Hsun Yang; Kazuki Hincks; Haobin Wang; Marino J E Resendiz
Journal:  Biopolymers       Date:  2020-11-20       Impact factor: 2.505
  5 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.