Macrolactamization of glycosylated peptide thioesters by the thioesterase domain of tyrocidine synthetase

Chemistry and Biology

Volumn 11, Issue 12, 2004, Pages 1635-1642

  Lin, Hening ^a   Thayer, Desiree A ^b   Wong, Chi Huey ^b   Walsh, Christopher T ^a  

^a HARVARD MEDICAL SCHOOL   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; ESTER; LACTAM; MACROCYCLIC COMPOUND; PEPTIDE; PEPTIDE SYNTHASE; THIOL ESTER HYDROLASE; TYROCIDINE; TYROCIDINE SYNTHETASE;

ARTICLE; BACILLUS SUBTILIS; CHEMISTRY; CONFORMATION; CYCLIZATION; DRUG EFFECT; DRUG SCREENING; ENZYME ACTIVE SITE; ENZYME SPECIFICITY; ERYTHROCYTE; GLYCOSYLATION; HUMAN; KINETICS; SYNTHESIS;

BACILLUS SUBTILIS; CATALYTIC DOMAIN; CYCLIZATION; DRUG EVALUATION, PRECLINICAL; ERYTHROCYTES; ESTERS; GLYCOSYLATION; HUMANS; KINETICS; LACTAMS; MACROCYCLIC COMPOUNDS; MOLECULAR CONFORMATION; PEPTIDE SYNTHASES; PEPTIDES; SUBSTRATE SPECIFICITY; THIOLESTER HYDROLASES; TYROCIDINE;

FELIS CATUS; ILEX COOKII;

EID: 10644233232     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2004.09.015     Document Type: Article

References (28)

1. C.T. Walsh Polyketide and nonribosomal peptide antibiotics: modularity and versatility Science 303 2004 1805 1810
2. R.M. Kohli, and C.T. Walsh Enzymology of acyl chain macrocyclization in natural product biosynthesis Chem. Commun. 7 2003 297 307
3. J.W. Trauger, R.M. Kohli, H.D. Mootz, M.A. Marahiel, and C.T. Walsh Peptide cyclization catalysed by the thioesterase domain of tyrocidine synthetase Nature 407 2000 215 218
4. C.C. Tseng, S.D. Bruner, R.M. Kohli, M.A. Marahiel, C.T. Walsh, and S.A. Sieber Characterization of the surfactin synthetase C-terminal thioesterase domain as a cyclic depsipeptide synthase Biochemistry 41 2002 13350 13359
5. S.A. Sieber, J. Tao, C.T. Walsh, and M.A. Marahiel Peptidyl thiophenols as substrates for nonribosomal peptide cyclases Angew. Chem. Int. Ed. Engl. 43 2004 493 498
6. J. Grunewald, S.A. Sieber, and M. Marahiel Chemo- and regioselective peptide cyclization triggered by the N-terminal fatty acid chain length: the recombinant cyclase of the calcium-dependent antibiotic from Streptomyces coelicolor Biochemistry 43 2004 2915 2925
7. R.M. Kohli, C.T. Walsh, and M.D. Burkart Biomimetic synthesis and optimization of cyclic peptide antibiotics Nature 418 2002 658 661
8. C.T. Walsh Combinatorial biosynthesis of antibiotics: challenges and opportunities ChemBioChem 3 2002 124 134
9. J. Staunton, and B. Wilkinson Biosynthesis of Erythromycin and Rapamycin Chem. Rev. 97 1997 2611 2630
10. R.J. Lewis, O.M. Singh, C.V. Smith, T. Skarzynski, A. Maxwell, A.J. Wonacott, and D.B. Wigley The nature of inhibition of DNA gyrase by the coumarins and the cyclothialidines revealed by X-ray crystallography EMBO J. 15 1996 1412 1420
11. H.C. Hosey, M.W. Peczuh, Z. Chen, U.S. Eggert, S.D. Dong, I. Pelczer, D. Kahne, and C.T. Walsh Tandem action of glycosyltransferases in the maturation of vancomycin and teicoplanin aglycones: novel glycopeptides Biochemistry 40 2001 4745 4755
12. H.C. Losey, J. Jiang, J.B. Biggins, M. Oberthur, X.Y. Ye, S.D. Dong, D. Kahne, J.S. Thorson, and C.T. Walsh Incorporation of glucose analogs by GtfE and GtfD from the vancomycin biosynthetic pathway to generate variant glycopeptides Chem. Biol. 9 2002 1305 1314
13. C.L.F. Meyers, M. Oberthur, J.W. Anderson, D. Kahne, and C.T. Walsh Initial characterization of novobiocic acid noviosyl transferase activity of NovM in biosynthesis of the antibiotic novobiocin Biochemistry 42 2003 4179 4189
14. W. Lu, C. Leimkuhler, M. Oberthür, D. Kahne, and C.T. Walsh AknK is an L-2-deoxyfucosyltransferase in the biosynthesis of the anthracycline aclacinomycin A Biochemistry 43 2004 4548 4558
15. W. Lu, M. Oberthur, C. Leimkuhler, J. Tao, D. Kahne, and C.T. Walsh Characterization of a regiospecific epivancosaminyl transferase GtfA and enzymatic reconstitution of the antibiotic chloroeremomycin Proc. Natl. Acad. Sci. USA 101 2004 4390 4395
16. J.W. Trauger, R.M. Kohli, and C.T. Walsh Cyclization of backbone-substituted peptides catalyzed by the thioesterase domain from the tyrocidine nonribosomal peptide synthetase Biochemistry 40 2001 7092 7098
17. R.M. Kohli, J.W. Trauger, D. Schwarzer, M.A. Marahiel, and C.T. Walsh Generality of peptide cyclization catalyzed by isolated thioesterase domains of nonribosomal peptide synthetases Biochemistry 40 2001 7099 7108
18. R.M. Kohli, J. Takagi, and C.T. Walsh The thioesterase domain from a nonribosomal peptide synthetase as a cyclization catalyst for integrin binding peptides Proc. Natl. Acad. Sci. USA 99 2002 1247 1252
19. R.M. Kohli, M.D. Burke, J. Tao, and C.T. Walsh Chemoenzymatic route to macrocyclid hybrid peptide/polyketide-like molecules J. Am. Chem. Soc. 125 2003 7160 7161
20. R.E.W. Hancock, and R. Lehrer Cationic peptides: a new source of antibiotics Trends Biotechnol. 16 1998 82 88
21. L.H. Kondejewski, S.W. Farmer, D.S. Wishart, C.M. Kay, R.E.W. Hancock, and R.S. Hodges Modulation of structure and antibacterial and hemolytic activity by ring size in cyclic gramicidin S analogs J. Biol. Chem. 271 1996 25261 25268
22. L.H. Kondejewski, M. Jelokhani-Niaraki, S.W. Farmer, B. Lix, C.M. Kay, B.D. Sykes, R.E.W. Hancock, and R.S. Hodges Dissociation of antimicrobial and hemolytic activities in cyclic peptide diastereomers by systematic alterations in amphipathicity J. Biol. Chem. 274 1999 13181 13192
23. H. Mootz, and M. Marahiel The tyrocidine biosynthesis operon of Bacillus brevis: complete nucleotide sequence and biochemical characterization of functional internal adenylation domains J. Bacteriol. 179 1997 6843 6850
24. C.T. Walsh, C.L.F. Meyers, and H.C. Losey Antibiotic glycosyltransferases: antibiotic maturation and prospects for reprogramming J. Med. Chem. 46 2003 3425 3436
25. S. Friedrich-Bochnitschek, H. Waldmann, and H. Kunz Allyl esters as carboxy protecting groups in the synthesis of O-glycopeptides J. Org. Chem. 54 1989 751 756
26. L.A. Salvador, M. Elofsson, and J. Kihlberg Preparation of building blocks for glycopeptide synthesis by glycosylation of Fmoc amino acids having unprotected carboxyl groups Tetrahedron 51 1995 5643 5656
27. N.E. Fahmi, S. Golovine, B. Wang, and S.M. Hecht Studies toward the site specific incorporation of sugars into proteins: synthesis of glycosylated aminoacyl-tRNAs Carbohydr. Res. 330 2001 149 164
28. U.K. Saha, and R.R. Schmidt Efficient synthesis of O-(2-acetamido-2- deoxy-β-D-glucopyranosyl)-serine and -threonine building blocks for glycopeptide formation J. Chem. Soc., Perkin Trans. 1 1 1997 1855 1860