Chapter 7 Formation and Characterization of Acyl Carrier Protein-Linked Polyketide Synthase Extender Units

Methods in Enzymology

Volumn 459, Issue B, 2009, Pages 143-163

  Chan, Yolande A ^a   Thomas, Michael G ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYL CARRIER PROTEIN; AMINOMALONYL ACYL CARRIER PROTEIN; ANTIBIOTIC AGENT; COENZYME A; HYDROXYMALONYL ACYL CARRIER PROTEIN; NITRILOTRIACETATE NICKEL; POLYKETIDE SYNTHASE; UNCLASSIFIED DRUG; ZWITTERMICIN A; PEPTIDE; RECOMBINANT PROTEIN;

ANTIBIOTIC BIOSYNTHESIS; BACILLUS CEREUS; ENZYME ANALYSIS; ENZYME PURIFICATION; ESTERIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; POLYACRYLAMIDE GEL ELECTROPHORESIS; POLYMERIZATION; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN MODIFICATION; PROTEIN PURIFICATION; REVIEW; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; GENETICS; MASS SPECTROMETRY; METABOLISM;

BACILLUS CEREUS;

ACYL CARRIER PROTEIN; BACILLUS CEREUS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ELECTROPHORESIS, POLYACRYLAMIDE GEL; MOLECULAR STRUCTURE; PEPTIDES; POLYKETIDE SYNTHASES; RECOMBINANT PROTEINS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 64049093901     PISSN: 00766879     EISSN: None     Source Type: Book Series    
DOI: 10.1016/S0076-6879(09)04607-2     Document Type: Review

References (24)

1. Byrne K.M., Shaflee A., Nielsen J., Arison B., Monaghan R.L., and Kaplan L. The biosynthesis and enzymology of an immunosuppressant, immunomycin, produced by Streptomyces hygroscopicus var, ascomyceticus. Dev. Ind. Microbiol. 32 (1993) 29-45
2. Carroll B.J., Moss S.J., Bai L., Kato Y., Toelzer S., Yu T.W., and Floss H.G. Identification of a set of genes involved in the formation of the substrate for the incorporation of the unusual "glycolate" chain extension unit in ansamitocin biosynthesis. J. Am. Chem. Soc. 124 (2002) 4176-4177
3. Chan Y.A., Boyne II M.T., Podevels A.M., Klimowicz A.K., Handelsman J., Kelleher N.L., and Thomas M.G. Hydroxymalonyl-acyl carrier protein (ACP). and aminomalonyl-ACP are two additional type I polyketide synthase extender units. Proc. Natl. Acad. Sci. USA 103 (2006) 14349-14354
4. Chan Y.A., Podevels A.M., Kevany B.M., and Thomas M.G. Biosynthesis of polyketide synthase extender units. Nat. Prod. Rep. 26 (2009) 90-114
5. Dorrestein P.C., Van Lanen S.G., Li W., Zhao C., Deng Z., Shen B., and Kelleher N.L. The bifunctional glyceryl transferase/phosphatase OzmB belonging to the HAD superfamily that diverts 1,3-bisphosphoglycerate into polyketide biosynthesis. J. Am. Chem. Soc. 128 (2006) 10386-10387
6. Gebhardt K., Schimana J., Müller J., Fiedler H.-P., Kallenborn H.G., Holzenkämpfer M., Krastel P., Zeeck A., Vater J., Höltzel A., Schmid D.G., Rheinheimer J., et al. Screening for biologically active metabolites with endosymbiotic bacilli isolated from arthropods. FEMS Microbiol. Lett. 217 (2002) 199-205
7. Gehring A.M., Bradley K.A., and Walsh C.T. Enterobactin biosynthesis in Escherichia coli: Isochorismate lyase (EntB) is a bifunctional enzyme that is phosphopantetheinylated by EntD and then acylated by EntE using ATP and 2,3-dihydroxybenzoate. Biochemistry 36 (1997) 8495-8503
8. Gokhale R.S., Tsuji S.Y., Cane D.E., and Khosla C. Dissecting and exploiting intermodular communication in polyketide synthases. Science 284 (1999) 482-485
9. Kato Y., Bai L., Xue Q., Revill W.P., Yu T.-W., and Floss H.G. Functional expression of genes involved in the biosynthesis of the novel polyketide chain extension unit, methoxymalonyl-acyl carrier protein, and engineered biosynthesis of 2-desmethyl-2-methoxy-6-deoxyerythronolide B. J. Am. Chem. Soc. 124 (2002) 5268-5269
10. Lambalot R.H., Gehring A.M., Flugel R.S., Zuber P., LaCelle M., Marahiel M.A., Reid R., Khosla C., and Walsh C.T. A new enzyme superfamily-the phosphopantetheinyl transferases. Chem. Biol. 3 (1996) 923-936
11. Lambalot R.H., and Walsh C.T. Holo-[acyl-carrier-protein] synthase of Escherichia coli. Methods Enzymol. 279 (1997) 254-262
12. Ligon J., Hill S., Beck J., Zirkle R., Molnár I., Zawodny J., Money S., and Schupp T. Characterization of the biosynthetic gene cluster for the antifungal polyketide soraphen A from Sorangium cellulosum So ce26. Gene 285 (2002) 257-267
13. Ono M., Sakuda S., Ikeda H., Furihata K., Nakayama J., Suzuki A., and Isogai A. Structures and biosynthesis of aflastatins: Novel inhibitors of aflatoxin production by Aspergillus parasiticus. J. Antibiot. 51 (1998) 1019-1028
14. Quadri L.E., Keating T.A., Patel H.M., and Walsh C.T. Assembly of the Pseudomonas aeruginosa nonribosomal peptide siderophore pyochelin: In vitro reconstitution of aryl-4, 2-bisthiazoline synthetase activity from PchD, PchE, and PchF. Biochemistry 38 (1999) 14941-14954
15. Quadri L.E., Weinreb P.H., Lei M., Nakano M.M., Zuber P., and Walsh C.T. Characterization of Sfp, a Bacillus subtilis phosphopantetheinyl transferase for peptidyl carrier protein domains in peptide synthetases. Biochemistry 37 (1998) 1585-1595
16. Reeves C.D., Chung L.M., Liu Y., Xue Q., Carney J.R., Revill W.P., and Katz L. A new substrate specificity for acyl transferase domains of the ascomycin polyketide synthase in Streptomyces hygroscopicus. J. Biol. Chem. 277 (2002) 9155-9159
17. Rude M.A., and Khosla C. Production of ansamycin polyketide precursors in Escherichia coli. J. Antibiot. 59 (2006) 464-470
18. Santi D.V., Webster Jr. R.W., and Cleland W.W. Kinetics of aminoacyl-tRNA synthetases catalyzed ATP-PPi exchange. Methods Enzymol. 29 (1974) 620-627
19. Schuhmann T., Vollmar D., and Grond S. Biosynthetic origin of the methoxyl extender unit in bafilomycin and concanamycin using stereospecifically labeled precursors. J. Antibiot. 60 (2007) 52-60
20. Shoji J., Sakazaki R., Wakisaka Y., Koizumi K., Mayama M., and Matsuura S. Isolation of galantins I and II, water-soluble basic peptides. Studies on antibiotics from the genus Bacillus. J. Antibiot. 28 (1975) 122-125
21. Walton L.J., Corre C., and Challis G.L. Mechanisms for incorporation of glycerol-derived precursors into polyketide metabolites. J. Ind. Microbiol. Biotechnol. 33 (2006) 105-120
22. Wenzel S.C., Williamson R.M., Grünanger C., Xu J., Gerth K., Martinez R.A., Moss S.J., Carroll B.J., Grond S., Unkefer C.J., Müller R., and Floss H.G. On the biosynthetic origin of methoxymalonyl-acyl carrier protein, the substrate for incorporation of "glycolate" units into ansamitocin and soraphen A. J. Am. Chem. Soc. 128 (2006) 14325-14336
23. Wu K., Chung L., Revill W.P., Katz L., and Reeves C.D. The FK520 gene cluster of Streptomyces hygroscopicus var. ascomyceticus (ATCC14891) contains genes for biosynthesis of unusual polyketide extender units. Gene 251 (2000) 81-90
24. Yu T.W., Bai L., Clade D., Hoffman D., Toelzer S., Trinh K.Q., Xu J., Moss S.J., Leistner E., and Floss H.G. The biosynthetic gene cluster of the maytansinoid antitumor agent ansamitocin from Actinosynnema pretiosum. Proc. Natl. Acad. Sci. USA 99 (2002) 7968-7973