Identification of the biosynthetic gene cluster for the pacidamycin group of peptidyl nucleoside antibiotics

Proceedings of the National Academy of Sciences of the United States of America

Volumn 107, Issue 39, 2010, Pages 16828-16833

  Zhang, Wenjun ^a,b   Ostash, Bohdan ^a,c   Walsh, Christopher T ^a  

^a HARVARD MEDICAL SCHOOL   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c IVAN FRANKO NATIONAL UNIVERSITY OF LVIV   (Ukraine)

Author keywords

Adenylation; Ureido bond; Uridine

Indexed keywords

PACIDAMYCIN; PEPTIDE SYNTHASE; POLYPEPTIDE ANTIBIOTIC AGENT; PROTEIN PACJ; PROTEIN PACL; PROTEIN PACN; PROTEIN PACO; PROTEIN PACP; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; PACIDAMYCIN 1; PEPTIDE; PYRIMIDINE NUCLEOSIDE;

ANTIBIOTIC BIOSYNTHESIS; ARTICLE; GENE CLUSTER; GENE DELETION; IN VITRO STUDY; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN EXPRESSION; STREPTOMYCES; STREPTOMYCES COERULEORUBIDUS; AMINO ACID SEQUENCE; BACTERIAL GENOME; BIOSYNTHESIS; CHEMISTRY; GENETICS; METABOLISM; MOLECULAR GENETICS; MULTIGENE FAMILY; PROTEIN TERTIARY STRUCTURE;

AGOUTI PACA; BACTERIA (MICROORGANISMS); STREPTOMYCES COERULEORUBIDUS;

AMINO ACID SEQUENCE; ANTI-BACTERIAL AGENTS; BASE SEQUENCE; GENE DELETION; GENOME, BACTERIAL; MOLECULAR SEQUENCE DATA; MULTIGENE FAMILY; PEPTIDES; PROTEIN STRUCTURE, TERTIARY; PYRIMIDINE NUCLEOSIDES; STREPTOMYCES;

EID: 78049295122     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1011557107     Document Type: Article

References (28)

1. Fronko RM, et al. (2000) New pacidamycins produced by Streptomyces coeruleorubidus, NRRL 18370. J Antibiot (Tokyo) 53:1405-1410.
2. Chen RH, Buko AM, Whittern DN, McAlpine JB (1989) Pacidamycins, a novel series of antibiotics with anti-Pseudomonas aeruginosa activity. II. Isolation and structural elucidation. J Antibiot (Tokyo) 42:512-520. (Pubitemid 19119087)
3. Muroi M, Kimura K, Osada H, Inukai M, Takatsuki A (1997) Liposidomycin B inhibits in vitro formation of polyprenyl (pyro)phosphate N-acetylglucosamine, an intermediate in glycoconjugate biosynthesis. J Antibiot (Tokyo) 50:103-104. (Pubitemid 27078069)
4. Tamura G, Sasaki T, Matsuhashi M, Takatsuki A, Yamasaki M (1976) Tunicamycin inhibits the formation of lipid intermediate in cell-free peptidoglycan synthesis of bacteria. Agric Biol Chem 40:447-449.
5. Hotoda H, et al. (2003) Synthesis and antimycobacterial activity of capuramycin analogues. Part 1: Substitution of the azepan-2-one moiety of capuramycin. Bioorg Med Chem Lett 13:2829-2832.
6. Hotoda H, et al. (2003) Synthesis and antimycobacterial activity of capuramycin analogues. Part 2: Acylated derivatives of capuramycin-related compounds. Bioorg Med Chem Lett 13:2833-2836.
7. McDonald LA, et al. (2002) Structures of the muraymycins, novel peptidoglycan biosynthesis inhibitors. J Am Chem Soc 124:10260-10261. (Pubitemid 34977365)
8. Isono F, Inukai M (1991) Mureidomycin A, a new inhibitor of bacterial peptidoglycan synthesis. Antimicrob Agents Chemother 35:234-236.
9. Chatterjee S, et al. (1994) Napsamycins, new Pseudomonas active antibiotics of the mureidomycin family from Streptomyces sp. HIL Y-82,11372. J Antibiot (Tokyo) 47:595-598. (Pubitemid 24166635)
10. Winn M, Goss RJ, Kimura K, Bugg TD (2010) Antimicrobial nucleoside antibiotics targeting cell wall assembly: Recent advances in structure-function studies and nucleoside biosynthesis. Nat Prod Rep 27:279-304.
11. Boojamra CG, et al. (2001) Stereochemical elucidation and total synthesis of dihydropacidamycin D, a semisynthetic pacidamycin. J Am Chem Soc 123:870-874.
12. Imker HJ, Walsh CT, Wuest WM (2009) SylC catalyzes ureido-bond formation during biosynthesis of the proteasome inhibitor syringolin A. J Am Chem Soc 131:18263-18265.
13. Chen W, et al. (2009) Characterization of the polyoxin biosynthetic gene cluster from Streptomyces cacaoi and engineered production of polyoxin H. J Biol Chem 284:10627-10638.
14. Kaysser L, et al. (2009) Identification and manipulation of the caprazamycin gene cluster lead to new simplified liponucleoside antibiotics and give insights into the biosynthetic pathway. J Biol Chem 284:14987-14996.
15. Kaysser L, Siebenberg S, Kammerer B, Gust B (2010) Analysis of the liposidomycin gene cluster leads to the identification of new caprazamycin derivatives. ChemBioChem 11:191-196.
16. Funabashi M, et al. (2009) Identification of the biosynthetic gene cluster of A-500359s in Streptomyces griseus SANK60196. J Antibiot (Tokyo) 62:325-332.
17. Lam WH, Rychli K, Bugg TD (2008) Identification of a novel beta-replacement reaction in the biosynthesis of 2,3-diaminobutyric acid in peptidylnucleoside mureidomycin A. Org Biomol Chem 6:1912-1917. (Pubitemid 351693235)
18. Rackham EJ, Gruschow S, Ragab AE, Dickens S, Goss RJ (2010) Pacidamycin biosynthesis: Identification and heterologous expression of the first uridyl peptide antibiotic gene cluster. ChemBioChem 11:1700-1709.
19. Muller C, et al. (2007) Sequencing and analysis of the biosynthetic gene cluster of the lipopeptide antibiotic Friulimicin in Actinoplanes friuliensis. Antimicrob Agents Chemother 51:1028-1037. (Pubitemid 46355291)
20. Jin M, Fischbach MA, Clardy J (2006) A biosynthetic gene cluster for the acetyl-CoA carboxylase inhibitor andrimid. J Am Chem Soc 128:10660-10661. (Pubitemid 44277738)
21. Heemstra JR, Jr, Walsh CT, Sattely ES (2009) Enzymatic tailoring of ornithine in the biosynthesis of the Rhizobium cyclic trihydroxamate siderophore vicibactin. J Am Chem Soc 131:15317-15329.
22. Lautru S, Oves-Costales D, Pernodet JL, Challis GL (2007) MbtH-like protein-mediated cross-talk between non-ribosomal peptide antibiotic and siderophore biosynthetic pathways in Streptomyces coelicolor M145. Microbiology 153:1405-1412. (Pubitemid 46779996)
23. Kieser T, Bibb MJ, Buttner MJ, Chater KF, Hopwood DA (2000) Practical Streptomyces Genetics (John Innes Foundation, Norwich, UK).
24. Gruschow S, et al. (2009) New pacidamycin antibiotics through precursor-directed biosynthesis. ChemBioChem 10:355-360.
25. Pfeifer BA, Admiraal SJ, Gramajo H, Cane DE, Khosla C (2001) Biosynthesis of complex polyketides in a metabolically engineered strain of E. coli. Science 291:1790-1792. (Pubitemid 32198984)
26. Yeh E, Kohli RM, Bruner SD, Walsh CT (2004) Type II thioesterase restores activity of a NRPS module stalled with an aminoacyl-S-enzyme that cannot be elongated. ChemBioChem 5:1290-1293. (Pubitemid 39297263)
27. Rausch C, Weber T, Kohlbacher O, Wohlleben W, Huson DH (2005) Specificity prediction of adenylation domains in nonribosomal peptide synthetases (NRPS) using transductive support vector machines (TSVMs). Nucleic Acids Res 33:5799-5808.
28. Gust B, Challis GL, Fowler K, Kieser T, Chater KF (2003) PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin. Proc Natl Acad Sci USA 100:1541-1546. (Pubitemid 36254483)