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Literature DB >> 2821489

Synthesis and resistance to enzymic hydrolysis of stereochemically-defined phosphonate and thiophosphate analogues of P1,P4-bis(5'-adenosyl) tetraphosphate.

G M Blackburn¹, G E Taylor, G R Thatcher, M Prescott, A G McLennan.

Abstract

Novel analogues of P1,P4-bis(5'-adenosyl) tetraphosphate, Ap4A (1), have been prepared with sulphur substituents at P1 and P4 and either oxygen or methylene bridges at the P2,P3-position. Separation of three isomers of the ApspCH2ppsA species has been achieved by a combination of mplc and hplc and the Rp,Rp, Rp,Sp, and Sp,Sp diastereoisomers identified on the basis of selective enzymatic hydrolysis using snake venom phosphodiesterase. Each of these three isomers is a strong competitive inhibitor of the specific Ap4Aase from Artemia and is highly resistant to the asymmetric cleavage normally catalysed by this enzyme.

Entities: Chemical Gene

Mesh：

Substances：

Year: 1987 PMID： 2821489 PMCID： PMC306188 DOI： 10.1093/nar/15.17.6991

Source DB: PubMed Journal: Nucleic Acids Res ISSN： 0305-1048 Impact factor: 16.971

43 in total

1. Stereochemical course of the reaction catalyzed by 5'-nucleotide phosphodiesterase from snake venom.

Authors: F R Bryant; S J Benkovic
Journal: Biochemistry Date: 1979-06-26 Impact factor: 3.162

2. Presence of diadenosine 5',5''' -P1, P4-tetraphosphate (Ap4A) in mamalian cells in levels varying widely with proliferative activity of the tissue: a possible positive "pleiotypic activator".

Authors: E Rapaport; P C Zamecnik
Journal: Proc Natl Acad Sci U S A Date: 1976-11 Impact factor: 11.205

3. Accumulation of dinucleoside polyphosphates in Saccharomyces cerevisiae under stress conditions. High levels are associated with cell death.

Authors: M Baltzinger; J P Ebel; P Remy
Journal: Biochimie Date: 1986 Oct-Nov Impact factor: 4.079

4. Absolute configuration of the diastereomers of adenosine 5'-O-(1-thiotriphosphate): consequences for the stereochemistry of polymerization by DNA-dependent RNA polymerase from Escherichia coli.

Authors: P M Burgers; F Eckstein
Journal: Proc Natl Acad Sci U S A Date: 1978-10 Impact factor: 11.205

5. Enzymatic synthesis of diadenosine tetraphosphate and diadenosine triphosphate with a purified lysyl-sRNA synthetase.

Authors: P C Zamecnik; M L Stephenson; C M Janeway; K Randerath
Journal: Biochem Biophys Res Commun Date: 1966-07-06 Impact factor: 3.575

6. Histone-dependent ADP-ribosylation of low molecular nucleotide by poly(ADP-ribose) polymerase.

Authors: Y Tanaka; N Matsunami; A Itaya; K Yoshihara
Journal: J Biochem Date: 1981-10 Impact factor: 3.387

7. Diadenosine tetraphosphate hydrolase from mouse liver. Purification to homogeneity and partial characterization.

Authors: M Höhn; W Albert; F Grummt
Journal: J Biol Chem Date: 1982-03-25 Impact factor: 5.157

8. Association of diadenosine 5',5"'-P1,P4-tetraphosphate binding protein with HeLa cell DNA polymerase alpha.

Authors: E Rapaport; P C Zamecnik; E F Baril
Journal: J Biol Chem Date: 1981-12-10 Impact factor: 5.157

9. Diadenosine 5',5'''-P1,P4-tetraphosphate, a ligand of the 57-kilodalton subunit of DNA polymerase alpha.

Authors: F Grummt; G Waltl; H M Jantzen; K Hamprecht; U Huebscher; C C Kuenzle
Journal: Proc Natl Acad Sci U S A Date: 1979-12 Impact factor: 11.205

10. Diadenosine 5',5'''-P1,P4-tetraphosphate triggers initiation of in vitro DNA replication in baby hamster kidney cells.

Authors: F Grummt
Journal: Proc Natl Acad Sci U S A Date: 1978-01 Impact factor: 11.205

14 in total

1. Antithrombotic effect of beta,beta'-monochloromethylene diadenosine 5',5"'-P1,P4-tetraphosphate.

Authors: B K Kim; P Zamecnik; G Taylor; M J Guo; G M Blackburn
Journal: Proc Natl Acad Sci U S A Date: 1992-11-15 Impact factor: 11.205

2. Adenosine-5'-O-phosphorylated and adenosine-5'-O-phosphorothioylated polyols as strong inhibitors of (symmetrical) and (asymmetrical) dinucleoside tetraphosphatases.

Authors: Andrzej Guranowski; Elzbieta Starzyńska; Alexander G McLennan; Janina Baraniak; Wojciech J Stec
Journal: Biochem J Date: 2003-07-15 Impact factor: 3.857

3. 2-MeS-beta,gamma-CCl2-ATP is a potent agent for reducing intraocular pressure.

Authors: Shay Eliahu; Alba Martín-Gil; María Jesús Perez de Lara; Jesús Pintor; Jean Camden; Gary A Weisman; Joanna Lecka; Jean Sévigny; Bilha Fischer
Journal: J Med Chem Date: 2010-04-22 Impact factor: 7.446

4. One-flask synthesis of dinucleoside tetra- and pentaphosphates.

Authors: Qianwei Han; Barbara L Gaffney; Roger A Jones
Journal: Org Lett Date: 2006-05-11 Impact factor: 6.005

5. Two hydrolase resistant analogues of diadenosine 5',5"'-P1,P3-triphosphate for studies with Fhit, the human fragile histidine triad protein.

Authors: G M Blackburn; X Liu; A Rösler; C Brenner
Journal: Nucleosides Nucleotides Date: 1998 Jan-Mar

6. Studies on some specific Ap4A-degrading enzymes with the use of various methylene analogues of P1P4-bis-(5',5'''-adenosyl) tetraphosphate.

Authors: A Guranowski; E Starzyńska; G E Taylor; G M Blackburn
Journal: Biochem J Date: 1989-08-15 Impact factor: 3.857