One-pot chemoenzymatic preparation of coenzyme A analogues

Analytical Biochemistry

Volumn 324, Issue 1, 2004, Pages 100-105

  Nazi, Ishac ^a   Koteva, Kalinka P ^a   Wright, Gerard D ^a  

^a MCMASTER UNIVERSITY   (Canada)

Author keywords

Coenzyme A; Dephosphocoenzyme A kinase; Pantothenate kinase; Pantothenic acid; Phosphopantotheine adenylyltransferase

Indexed keywords

AMINO ACIDS; ESCHERICHIA COLI;

ADENYLYLTRANSFERASE; COENZYME A; DEPHOSPHOCOENZYME A KINASE; PANTOTHENATE KINASE; PANTOTHENIC ACID;

COENZYMES;

4 AMINOBUTYRIC ACID ETHYLTHIOESTER; ACID; BACTERIAL ENZYME; COENZYME A; HISTIDINE DERIVATIVE; N ALPHA TERT BUTYLOXYCARBONYL 4 AMINOBUTYRIC ACID; N ALPHA TERT BUTYLOXYCARBONYL 4 AMINOBUTYRIC ACID ETHYLTHIOESTER; N ALPHA TERT BUTYLOXYCARBONYL 4 AMINOBUTYRIC ACID METHYL ESTER; PANTOTHENATE KINASE; PANTOTHENYL 4 AMIDOBUTYRATE 1 ETHYLTHIOESTER; PANTOTHENYL 4 AMIDOBUTYRATE 1 METHYL ESTER; PANTOTHENYL 4 AMIDOBUTYRATE 1 PROPYLTHIOESTER; PANTOTHENYL O PIVALOYLOXY 2 AMIDETHANOL; PANTOTHENYL O PIVALOYLOXY 4 AMIDOBUTANOL; PHOSPHOTRANSFERASE; PROTEIN; TRANSFERASE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; ENZYME SYNTHESIS; ESCHERICHIA COLI; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; STOICHIOMETRY;

ESCHERICHIA COLI;

EID: 0344925050     PISSN: 00032697     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ab.2003.09.005     Document Type: Article

References (19)

1. Lee C.H., Chen A.F. Immobilized coenzymes and derivatives. Everse J., Anderson B., You K. The Pyridine Nucleotide Coenzymes. 1982;189 Academic Press, New York.
2. Mishra P.K., Drueckhammer D.G. Coenzyme A analogues and derivatives: synthesis and applications as mechanistic probes of coenzyme A ester-utilizing enzymes. Chem. Rev. 100:2000;3283-3310.
3. Hebert R.B. Biosynthesis of Secondary Metabolites. 1981;Chapman & Hall, London. pp. 28-44.
4. Shaw W.V. Chloramphenicol acetyltransferase: enzymology and molecular biology. CRC Crit. Rev. Biochem. 14:1983;1-46.
5. Wright G.D. Aminoglycoside-modifying enzymes. Curr. Opin. Microbiol. 2:1999;499-503.
6. Johnston N.J., Mukhtar T.A., Wright G.D. Streptogramin antibiotics: mode of action and resistance. Curr. Drug Targets. 3:2002;335-344.
7. Walsh C.T., Gehring A.M., Weinreb P.H., Quadri L.E., Flugel R.S. Post-translational modification of polyketide and nonribosomal peptide synthases. Curr. Opin. Chem. Biol. 1:1997;309-315.
8. Ouyang T., Walt D.R. A new chemical method for synthesizing and recycling acyl coenzyme A thioesters. J. Org. Chem. 56:1991;3752-3755.
9. Billhardt U.M., Stein P., Whitesides G.M. Bioorg. Chem. 17:1989;1-12.
10. Martin D.P., Bibart R.T., Drueckhammer D.G. Synthesis of novel analogs of acetyl coenzyme A: mimics of enzyme reaction intermediates. J. Am. Chem. Soc. 116:1994;4660-4668.
11. Vogel K.W., Drueckhammer D.G. A reversed thioester analogue of acetyl-coenzyme A: an inhibitor of thiolase and a synthon for other acyl-coA analogues. J. Am. Chem. Soc. 120:1998;3275-3283.
12. Bibart R.T., Vogel K.W., Drueckhammer D.G. Development of a second generation coenzyme A analogue synthon. J. Org. Chem. 64:1999;2903-2909.
13. Vogel K.W., Stark L.M., Mishra P.K., Yang W., Drueckhammer D.G. Investigating the role of the geminal dimethyl groups of coenzyme A: synthesis and studies of a didemethyl analogue. Bioorg. Med. Chem. 8:2000;2451-2460.
14. Bodanszky M. Principles of Peptide Synthesis. 1984;Springer-Verlag, Berlin.
15. Kim S., Kim Y.C., Lee J.I. A new convenient method for the esterification of carboxylic acids. Tetrahedr. Lett. 24:1983;3365-3368.
16. Miyano M., Deason J.R., Nakao A., Stealey M.A., Villamil C.I., Sohn D.D., Mueller R. (Acyloxy)benzophenones and (acyloxy)-4-pyrones. A new class of inhibitors of human neutrophil elastase. J. Med. Chem. 31:1988;1052-1061.
17. Song W.J., Jackowski S. Cloning, sequencing, and expression of the pantothenate kinase (coaA) gene of Escherichia coli. J. Bacteriol. 174:1992;6411-6417.
18. Geerlof A., Lewendon A., Shaw W.V. Purification and characterization of phosphopantotheine adenylyltransferase from Escherichia coli. J. Biol. Chem. 274:1999;27105-27111.
19. Mishra P., Park P.K., Drueckhammer D.G. Identification of yacE (coaE) as the structural gene for dephosphocoenzyme A kinase in Escherichia coli K-12. J. Bacteriol. 183:2001;2774-2778.