Recognition of (2 S)-aminomalonyl-acyl carrier protein (ACP) and (2 R)-hydroxymalonyl-ACP by acyltransferases in zwittermicin A biosynthesis

Biochemistry

Volumn 49, Issue 17, 2010, Pages 3667-3677

  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 PROTEINS; ACYLTRANSFERASES; COENZYME A; COMBINATORIAL BIOSYNTHESIS; L-SERINE; POLYKETIDE SYNTHASES; POLYKETIDES; PRIMARY METABOLITE; SUBSTRATE SELECTIVITY;

AMINO ACIDS; BIOCHEMISTRY; BIOSYNTHESIS; CARBOXYLIC ACIDS; ORGANIC ACIDS; PHOSPHATASES; PLANTS (BOTANY); SULFUR COMPOUNDS;

PROTEINS;

ACYL CARRIER PROTEIN; ACYLTRANSFERASE; AMINOMALONYL ACYL CARRIER PROTEIN; ANTIBIOTIC AGENT; ENZYME; HYDROXYMALONYL ACYL CARRIER PROTEIN; POLYKETIDE SYNTHASE; UNCLASSIFIED DRUG; ZWITTERMICIN A; AMINOMALONIC ACID; MALONIC ACID DERIVATIVE; PEPTIDE; TARTRONIC ACID; TARTRONIC ACID DERIVATIVE;

ANIMAL CELL; ARTICLE; BIOSYNTHESIS; CHEMICAL ANALYSIS; COMPLEX FORMATION; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME SPECIFICITY; METABOLITE; MOLECULAR RECOGNITION; NONHUMAN; PRIORITY JOURNAL; PROTEIN TRANSPORT; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; MASS SPECTROMETRY; METABOLISM; PLASMID; STEREOISOMERISM;

ACYL CARRIER PROTEIN; ACYLTRANSFERASES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MALONATES; PEPTIDES; PLASMIDS; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; STEREOISOMERISM; TARTRONATES;

EID: 77951685700     PISSN: 00062960     EISSN: 15204995     Source Type: Journal    
DOI: 10.1021/bi100141n     Document Type: Article

References (29)

1. Cane, D. E., Walsh, C. T., and Khosla, C. (1998) Harnessing the biosynthetic code: Combinations, permutations, and mutations Science 282, 63-68
2. Staunton, J. and Weissman, K. J. (2001) Polyketide biosynthesis: A millennium review Nat. Prod. Rep. 18, 380-416
3. Khosla, C., Gokhale, R. S., Jacobsen, J. R., and Cane, D. E. (1999) Tolerance and specificity of polyketide synthases Annu. Rev. Biochem. 68, 219-253
4. Fujimori, D. G. and Walsh, C. T. (2007) What's new in enzymatic halogenations Curr. Opin. Chem. Biol. 11, 553-560
5. Walsh, C. T. (2002) Combinatorial biosynthesis of antibiotics: Challenges and opportunities ChemBioChem 3, 124-134
6. Moore, B. S. and Hertweck, C. (2002) Biosynthesis and attachment of novel bacterial polyketide synthase starter units Nat. Prod. Rep. 19, 70-99
7. Chan, Y. A., Podevels, A. M., Kevany, B. M., and Thomas, M. G. (2009) Biosynthesis of polyketide synthase extender units Nat. Prod. Rep. 26, 90-114
8. Liu, Y., Hazzard, C., Eustáquio, A. S., Reynolds, K. A., and Moore, B. S. (2009) Biosynthesis of salinosporamides from α,β- unsaturated fatty acids: Implications for extending polyketide synthase diversity J. Am. Chem. Soc. 131, 10376-10377
9. Wu, K., Chung, L., Revill, W. D., Katz, L., and Reeves, C. D. (2000) The FK520 gene cluster of Streptomyces hygroscopicus var. ascomyceticus (ATCC14891) contains genes for biosynthesis of unusual polyketide extender units Gene 251, 81-90
10. 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. (2002) The biosynthetic gene cluster of the maytansinoid antitumor agent ansamitocin from Actinosynnema pretiosum Proc. Natl. Acad. Sci. U.S.A. 99, 7968-7973
11. Ligon, J., Hill, S., Beck, J., Zirkle, R., Molnár, I., Zawodny, J., Money, S., and Schupp, T. (2002) Characterization of the biosynthetic gene cluster for the antifungal polyketide soraphen A from Sorangium cellulosum So ce26 Gene 285, 257-267
12. Chan, Y. A., Boyne, M. T., II, Podevels, A. M., Klimowicz, A. K., Handelsman, J., Kelleher, N. L., and Thomas, M. G. (2006) Hydroxymalonyl-acyl carrier protein (ACP) and aminomalonyl-ACP are two additional type I polyketide synthase extender units Proc. Natl. Acad. Sci. U.S.A. 103, 14349-14354
13. Rachid, S., Scharfe, M., Blöcker, H., Weissman, K. J., and Müller, R. (2009) Unusual chemistry in the biosynthesis of the antibiotic chondrochlorens Chem. Biol. 16, 70-81
14. Broderick, N. A., Goodman, R. M., Raffa, K. F., and Handelsman, J. (2000) Synergy between zwittermicin A and Bacillus thuringiensis subsp. kurstaki against gypsy moth (Lepidoptera: Lymantriidae) Environ. Entomol. 29, 101-107
15. Silo-Suh, L. A., Lethbridge, B. J., Raffel, S. J., He, H., Clardy, J., and Handelsman, J. (1994) Biological activities of two fungistatic antibiotics produced by Bacillus cereus UW85 Appl. Environ. Microbiol. 60, 2023-2030
16. Silo-Suh, L. A., Stabb, E. V., Raffel, S. J., and Handelsman, J. (1998) Target range of zwittermicin A, an aminopolyol antibiotic from Bacillus cereus Curr. Microbiol. 37, 6-11
17. Kato, Y., Bai, L., Xue, Q., Revill, W. P., Yu, T.-W., and Floss, H. G. (2002) 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, 5268-5269
18. Ruan, X., Pereda, A., Stassi, D. L., Zeidner, D., Summers, R. G., Jackson, M., Shivakumar, A., Kakavas, S., Staver, M. J., Donadio, S., and Katz, L. (1997) Acyltransferase domain substitutions in erythromycin polyketide synthase yield novel erythromycin derivatives J. Bacteriol. 179, 6416-6425
19. Emmert, E. A. B., Klimowicz, A. K., Thomas, M. G., and Handelsman, J. (2004) Genetics of zwittermicin A production by Bacillus cereus Appl. Environ. Microbiol. 70, 104-113
20. Kevany, B. M., Rasko, D. A., and Thomas, M. G. (2009) Characterization of the complete zwittermicin A biosynthesis gene cluster from Bacillus cereus Appl. Environ. Microbiol. 75, 1144-1155
21. Cheng, Y. Q., Tang, G. L., and Shen, B. (2003) Type I polyketide synthase requiring a discrete acyltransferase for polyketide biosynthesis Proc. Natl. Acad. Sci. U.S.A. 100, 3149-3154 (Pubitemid 36356554)
22. Chan, Y. A. and Thomas, M. G. (2009) Formation and characterization of acyl carrier protein-linked polyketide synthase extender units Methods Enzymol. 459, 143-163
23. Liou, G. F., Lau, J., Cane, D. E., and Khosla, C. (2003) Quantitative analysis of loading and extender unit acyltransferases of modular polyketide synthases Biochemistry 42, 200-207
24. Joshi, V. C. (1972) Mechanism of malonyl-coenzyme A-acyl carrier protein transacylase Biochem. J. 128, 43-44
25. Keatinge-Clay, A. T., Shelat, A. A., Savage, D. F., Tsai, S.-C., Miercke, L. J. W., O'Connell, J. D., III, Khosla, C., and Stroud, R. M. (2003) Catalysis, specificity, and ACP docking site of Streptomyces coelicolor malonyl-CoA:ACP transacylase Structure 11, 147-154
26. Reeves, C. D., Chung, L. M., Liu, Y., Xue, Q., Carney, J. R., Revill, W. P., and Katz, L. (2002) A new substrate specificity for acyl transferase domains of the ascomycin polyketide synthase in Streptomyces hygroscopicus J. Biol. Chem. 277, 9155-9159
27. Roujeinikova, A., Simon, W. J., Gilroy, J., Rice, D. W., Rafferty, J. B., and Slabas, A. R. (2007) Structural studies of fatty acyl-(acyl carrier protein) thioesters reveal a hydrophobic binding cavity that can expand to fit longer substrates J. Mol. Biol. 365, 135-145
28. Lopanik, N. B., Shields, J. A., Bucholz, T. J., Rath, C. M., Hothersall, J., Haygood, M. G., Häkansson, K., Thomas, C. M., and Sherman, D. H. (2008) In vivo and in vitro transacylation by BryP, the putative bryostatin pathway acyltransferase derived from an uncultured marine symbiont Chem. Biol. 15, 1175-1186
29. Tang, G. L., Cheng, Y. Q., and Shen, B. (2004) Leinamycin biosynthesis revealing unprecedented architectural complexity for a hybrid polyketide synthase and nonribosomal peptide synthetase Chem. Biol. 11, 33-45