Combining biocatalysis and chemoselective chemistries for glycopeptide antibiotics modification

Current Opinion in Chemical Biology

Volumn 16, Issue 1-2, 2012, Pages 170-178

  Li, Tsung Lin ^a   Liu, Yu Chen ^a   Lyu, Syue Yi ^a  

^a GENOMICS RESEARCH CENTER   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

3,5 DIHYDROXYPHENYLGLYCINE; BALHIMYCIN; COMPLESTATIN; DALBAVANCIN; DECHLOROEREMOMYCIN; GLYCOPEPTIDE; GLYCOSYLTRANSFERASE; HEPTAPEPTIDE; INORGANIC PYROPHOSPHATASE; ORITAVANCIN; OXFENICINE; POLYPEPTIDE ANTIBIOTIC AGENT; PYRUVATE KINASE; SULFOTRANSFERASE; TEICOPLANIN; TELAVANCIN; VANCOMYCIN;

ACYLATION AND DEACYLATION; BIOCATALYSIS; BIOSYNTHESIS; CRYSTAL STRUCTURE; DECHLORINATION; ENGINEERING; FLUORINATION; GENE CLUSTER; GLYCOSYLATION; GRAM POSITIVE INFECTION; HELICOBACTER PYLORI; IN VITRO STUDY; IN VIVO STUDY; MUTAGENESIS; NONHUMAN; PASTEURELLA MULTOCIDA; PROTEIN DATA BANK; PROTEIN ENGINEERING; REVIEW;

ANTI-BACTERIAL AGENTS; BIOCATALYSIS; GLYCOPEPTIDES; OXIDATION-REDUCTION;

BACTERIA (MICROORGANISMS); POSIBACTERIA;

EID: 84862817770     PISSN: 13675931     EISSN: 18790402     Source Type: Journal    
DOI: 10.1016/j.cbpa.2012.01.017     Document Type: Review

References (57)

1. Schreiber S.L. Target-oriented and diversity-oriented organic synthesis in drug discovery. Science 2000, 287:1964-1969.
2. Nicolaou K.C., Pfefferkorn J.A., Roecker A.J., Cao G.-Q., Barluenga S., Mitchell H.J. Natural product-like combinatorial libraries based on privileged structures. 1. General principles and solid-phase synthesis of benzopyrans. J Am Chem Soc 2000, 122:9939-9953.
3. Linden P.K. Vancomycin resistance: are there better glycopeptides coming?. Expert Rev Anti Infect Ther 2008, 6:917-928.
4. Murray B.E. Vancomycin-resistant enterococcal infections. N Engl J Med 2000, 342:710-721.
5. Roecker A.M., Pope S.D. Dalbavancin: a lipoglycopeptide antibacterial for Gram-positive infections. Expert Opin Pharmacother 2008, 9:1745-1754.
6. Leonard S.N., Rybak M.J. Telavancin: an antimicrobial with a multifunctional mechanism of action for the treatment of serious gram-positive infections. Pharmacotherapy 2008, 28:458-468.
7. Poulakou G., Giamarellou H. Oritavancin: a new promising agent in the treatment of infections due to Gram-positive pathogens. Expert Opin Investig Drugs 2008, 17:225-243.
8. Arias C.A., Murray B.E. Antibiotic-resistant bugs in the 21st century - a clinical super-challenge. N Engl J Med 2009, 360:439-443.
9. Payne D.J., Gwynn M.N., Holmes D.J., Pompliano D.L. Drugs for bad bugs: confronting the challenges of antibacterial discovery. Nat Rev Drug Discov 2007, 6:29-40.
10. Nicolaou K.C., Boddy C.N., S S.B., Winssinger N. Chemistry, biology, and medicine of the glycopeptide antibiotics. Angew Chem Int Ed Engl 1999, 38:2096-2152.
11. Pelzer S., Süssmuth R., Heckmann D., Recktenwald J., Huber P., Jung G., Wohlleben W. Identification and analysis of the balhimycin biosynthetic gene cluster and its use for manipulating glycopeptide biosynthesis in Amycolatopsis mediterranei DSM5908. Antimicrob Agents Chemother 1999, 43:1565-1573.
12. Wageningen A.M.v., Kirkpatrick P.N., Williams D.H., Harris B.R., Kershaw J.K., Lennard N.J., M M.J., Jones S.J., Solenberg P.J. Sequencing and analysis of genes involved in the biosynthesis of a vancomycin group antibiotic. Chem Biol 1998, 5:155-162.
13. Chiu H.T., Hubbard B.K., Shah A.N., Eide J., Fredenburg R.A., Walsh C.T., Khosla C. Molecular cloning and sequence analysis of the complestatin biosynthetic gene cluster. Proc Natl Acad Sci USA 2001, 98:8548-8553.
14. Pootoolal J., Thomas M.G., Marshall C.G., Neu J.M., Hubbard B.K., Walsh C.T., Wright G.D. Assembling the glycopeptide antibiotic scaffold: the biosynthesis of A47934 from Streptomyces toyocaensis NRRL15009. Proc Natl Acad Sci USA 2002, 99:8962-8967.
15. Sosio M., Stinchi S., Beltrametti F., Lazzarini A., Donadio S. The gene cluster for the biosynthesis of the glycopeptide antibiotic A40926 by nonomuraea species. Chem Biol 2003, 10:541-549.
16. Sosio M., Kloosterman H., Bianchi A., Vreugd P.d., Dijkhuizen L., Donadio S. Organization of the teicoplanin gene cluster in Actinoplanes teichomyceticus. Microbiology 2004, 150:95-102.
17. Li T.L., Huang F., Haydock S.F., Mironenko T., Leadlay P.F., Spencer J.B. Biosynthetic gene cluster of the glycopeptide antibiotic teicoplanin: characterization of two glycosyltransferases and the key acyltransferase. Chem Biol 2004, 11:107-119.
18. Banik J.J., Brady S.F. Cloning and characterization of new glycopeptide gene clusters found in an environmental DNA megalibrary. Proc Natl Acad Sci USA 2008, 105:17273-17277.
19. Kahne D., Leimkuhler C., Lu W., Walsh C.T. Glycopeptide and lipoglycopeptide antibiotics. Chem Rev 2005, 105:425-448.
20. Stegmann E., Frasch H.J., Wohlleben W. Glycopeptide biosynthesis in the context of basic cellular functions. Curr Opin Microbiol 2010, 13:595-602.
21. Sosio M., Donadio S. Understanding and manipulating glycopeptide pathways: the example of the dalbavancin precursor A40926. J Ind Microbiol Biotechnol 2006, 33:569-576.
22. Donadio S., Sosio M. Biosynthesis of glycopeptides: prospects for improved antibacterials. Curr Top Med Chem 2008, 8:654-666.
23. Hubbard B.K., Walsh C.T. Vancomycin assembly: nature's way. Angew Chem Int Ed Engl 2003, 42:730-765.
24. Bick M.J., Banik J.J., Darst S.A., Brady S.F. Crystal structures of the glycopeptide sulfotransferase Teg12 in a complex with the teicoplanin aglycone. Biochemistry 2010, 49:4159-4168.
25. Bick M.J., Banik J.J., Darst S.A., Brady S.F. The 2.7 å resolution structure of the glycopeptide sulfotransferase Teg14. Acta Crystallogr D Biol Crystallogr 2010, 66:1278-1286.
26. Shi R., Lamb S.S., Bhat S., Sulea T., Wright G.W., Matte A., Cygler M. Crystal structure of StaL, a glycopeptide antibiotic sulfotransferase from Streptomyces toyocaensis. J Biol Chem 2007, 282:13073-13086.
27. Gantt R.W., Peltier-Pain P., Thorson J.S. Enzymatic methods for glyco(diversification/randomization) of drugs and small molecules. Nat Prod Rep 2011, 28:1811-1853.
28. Luzhetskyy A., Bechthold A. Features and applications of bacterial glycosyltransferases: current state and prospects. Appl Microbiol Biotechnol 2008, 80:945-952.
29. Langenhan J.M., Griffith B.R., Thorson J.S. Neoglycorandomization and chemoenzymatic glycorandomization: two complementary tools for natural product diversification. J Nat Prod 2005, 68:1696-1711.
30. Losey H.C., Peczuh M.W., Chen Z., Eggert U.S., Dong S.D., Pelczer I., Kahne D., Walsh C.T. Tandem action of glycosyltransferases in the maturation of vancomycin and teicoplanin aglycones: novel glycopeptides. Biochemistry 2001, 40:4745-4755.
31. Solenberg PJ M.P., Stack D.R., Wilkie S.C., Thompson R.C., Baltz R.H. Production of hybrid glycopeptide antibiotics in vitro and in Streptomyces toyocaensis. Chem Biol 1997, 4:195-202.
32. Mulichak A.M., Lu W., Losey H.C., Walsh C.T., Garavito R.M. Crystal structure of vancosaminyltransferase GtfD from the vancomycin biosynthetic pathway: interactions with acceptor and nucleotide ligands. Biochemistry 2004, 43:5170-5180.
33. Mulichak A.M., Losey H.C., Lu W., Wawrzak Z., Walsh C.T., Garavito R.M. Structure of the TDP-epi-vancosaminyltransferase GtfA from the chloroeremomycin biosynthetic pathway. Proc Natl Acad Sci USA 2003, 100:9238-9243.
34. Mulichak A.M., Losey H.C., Walsh C.T., Garavito R.M. Structure of the UDP-glucosyltransferase GtfB that modifies the heptapeptide aglycone in the biosynthesis of vancomycin group antibiotics. Structure 2001, 9:547-557.
35. Fu X., Albermann C., Jiang J., Liao J., Zhang C., Thorson J.S. Antibiotic optimization via in vitro glycorandomization. Nat Biotechnol 2003, 21:1467-1469.
36. Ritter T.K., Mong K.K., Liu H., Nakatani T., Wong C.H. A programmable one-pot oligosaccharide synthesis for diversifying the sugar domains of natural products: a case study of vancomycin. Angew Chem Int Ed Engl 2003, 42:4657-4660.
37. Thayer D.A., Wong C.H. Vancomycin analogues containing monosaccharides exhibit improved antibiotic activity: a combined one-pot enzymatic glycosylation and chemical diversification strategy. Chem Asian J 2006, 1:445-452.
38. Oh T.J.K.D., Kang S.Y., Yamaguchi T., Sohng J.K. Enzymatic synthesis of vancomycin derivatives using galactosyltransferase and sialyltransferase. J Antibiot (Tokyo) 2011, 64:103-109.
39. Breton C., Snajdrová L., Jeanneau C., Koca J., Imberty A. Structures and mechanisms of glycosyltransferases. Glycobiology 2006, 16:29R-37R.
40. Park S.H., Park H.Y., Sohng J.K., Lee H.C., Liou K., Yoon Y.J., Kim B.G. Expanding substrate specificity of GT-B fold glycosyltransferase via domain swapping and high-throughput screening. Biotechnol Bioeng 2009, 102:988-994.
41. Truman A.W., Dias M.V., Wu S., Blundell T.L., Huang F., Spencer J.B. Chimeric glycosyltransferases for the generation of hybrid glycopeptides. Chem Biol 2009, 16:676-685.
42. Zhang C., Griffith B.R., Fu Q., Albermann C., Fu X., Lee I.K., Li L., Thorson J.S. Exploiting the reversibility of natural product glycosyltransferase-catalyzed reactions. Science 2006, 313:1291-1294.
43. Gantt R.W., Peltier-Pain P., Cournoyer W.J., Thorson J.S. Using simple donors to drive the equilibria of glycosyltransferase-catalyzed reactions. Nat Chem Biol 2011, 7:685-691.
44. Ho J.Y., Huang Y.T., Wu C.J., Li Y.S., Tsai M.D., Li T.L. Glycopeptide biosynthesis: Dbv21/Orf2 from dbv/tcp gene clusters are N-Ac-Glm teicoplanin pseudoaglycone deacetylases and Orf15 from cep gene cluster is a Glc-1-P thymidyltransferase. J Am Chem Soc 2006, 128:13694-13695.
45. Truman A.W., Robinson L., Spencer J.B. Identification of a deacetylase involved in the maturation of teicoplanin. Chembiochem 2006, 7:1670-1675.
46. Howard-Jones A.R., Kruger R.G., Lu W., Tao J., Leimkuhler C., Kahne D., Walsh C.T. Kinetic analysis of teicoplanin glycosyltransferases and acyltransferase reveal ordered tailoring of aglycone scaffold to reconstitute mature teicoplanin. J Am Chem Soc 2007, 129:10082-10083.
47. Kruger R.G., Lu W., Oberthür M., Tao J., Kahne D., Walsh C.T. Tailoring of glycopeptide scaffolds by the acyltransferases from the teicoplanin and A-40,926 biosynthetic operons. Chem Biol 2005, 12:131-140.
48. * crystal structures. Mol Biosyst 2011, 7:1224-1231.
49. Li Y.S., Ho J.Y., Huang C.C., Lyu S.Y., Lee C.Y., Huang Y.T., Wu C.J., Chan H.C., Huang C.J., Hsu N.S., et al. A unique flavin mononucleotide-linked primary alcohol oxidase for glycopeptide A40926 maturation. J Am Chem Soc 2007, 129:13384-13385.
50. Liu Y.C., Li Y.S., Lyu S.Y., Hsu L.J., Chen Y.H., Huang Y.T., Chan H.C., Huang C.J., Chen G.H., Chou C.C., et al. Interception of teicoplanin oxidation intermediates yields new antimicrobial scaffolds. Nat Chem Biol 2011, 7:304-309.
51. O'Briena D.P., Kirkpatricka P.N., O'Briena S.W., Staroske T., Richardsonb T.I., Evansb D.A., Hopkinsonc A., Spencera J.B., Williams D.H. Expression and assay of an N-methyltransferase involved in the biosynthesis of a vancomycin group antibiotic. Chem Commun 2000, 103-104.
52. Shi R., Lamb S.S., Zakeri B., Proteau A., Cui Q., Sulea T., Matte A., Wright G.D., Cygler M. Structure and function of the glycopeptide N-methyltransferase MtfA, a tool for the biosynthesis of modified glycopeptide antibiotics. Chem Biol 2009, 16:401-410.
53. Weist S., Süssmuth R.D. Mutational biosynthesis - a tool for the generation of structural diversity in the biosynthesis of antibiotics. Appl Microbiol Biotechnol 2005, 68:141-150.
54. Puk O., Huber P., Bischoff D., Recktenwald J., Jung G., Süssmuth R.D., Pée K.H.v., Wohlleben W., Pelzer S. Glycopeptide biosynthesis in Amycolatopsis mediterranei DSM5908: function of a halogenase and a haloperoxidase/perhydrolase. Chem Biol 2002, 9:225-235.
55. Weist S., Bister B., Puk O., Bischoff D., Pelzer S., Nicholson G.J., Wohlleben W., Jung G., Süssmuth R.D. Fluorobalhimycin - a new chapter in glycopeptide antibiotic research. Angew Chem Int Ed Engl 2002, 41:3383-3385.
56. Weist S., Kittel C., Bischoff D., Bister B., Pfeifer V., Nicholson G.J., Wohlleben W., Süssmuth R.D. Mutasynthesis of glycopeptide antibiotics: variations of vancomycin's AB-ring amino acid 3,5-dihydroxyphenylglycine. J Am Chem Soc 2004, 126:5942-5943.
57. Stinchi S., Carrano L., Lazzarini A., Feroggio M., Grigoletto A., Sosio M., Donadio S. A derivative of the glycopeptide A40926 produced by inactivation of the beta-hydroxylase gene in Nonomuraea sp. ATCC39727. FEMS Microbiol Lett 2006, 256:229-235.