Complete set of glycosyltransferase structures in the calicheamicin biosynthetic pathway reveals the origin of regiospecificity

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

Volumn 108, Issue 43, 2011, Pages 17649-17654

  Chang, Aram ^a   Singh, Shanteri ^a   Helmich, Kate E ^a   Goff, Randal D ^a   Bingman, Craig A ^a   Thorson, Jon S ^a   Phillips Jr , George N ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALICHEAMICIN DERIVATIVE; CALICHEAMICIN GLYCOSYLTRANSFERASE1; CALICHEAMICIN GLYCOSYLTRANSFERASE2; CALICHEAMICIN GLYCOSYLTRANSFERASE3; CALICHEAMICIN GLYCOSYLTRANSFERASE4; GLYCOSYLTRANSFERASE; HYDROXYLAMINE; NATURAL PRODUCT; SUGAR; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BIOSYNTHESIS; CARBOXY TERMINAL SEQUENCE; CATALYSIS; ENZYME ACTIVE SITE; ENZYME MECHANISM; ENZYME STRUCTURE; GLYCOSYLATION; PRIORITY JOURNAL; PROTEIN MOTIF; SIGNAL TRANSDUCTION; STEREOCHEMISTRY;

AMINOGLYCOSIDES; ANTIBIOTICS, ANTINEOPLASTIC; CARBOHYDRATES; ENEDIYNES; GLYCOSYLTRANSFERASES; HYDROXYLAMINES; PROTEIN ENGINEERING; PROTEIN INTERACTION DOMAINS AND MOTIFS;

EID: 80055072048     PISSN: 00278424     EISSN: 10916490     Source Type: Journal    
DOI: 10.1073/pnas.1108484108     Document Type: Article

References (41)

1. Walsh CT, Fischbach MA (2010) Natural products version 2.0: Connecting genes to molecules. J Am Chem Soc 132:2469-2493.
2. Weymouth-Wilson AC (1997) The role of carbohydrates in biologically active natural products. Nat Prod Rep 14:99-110.
3. Thibodeaux CJ, Melancon CE, Liu HW (2007) Unusual sugar biosynthesis and natural product glycodiversification. Nature 446:1008-1016. (Pubitemid 46676062)
4. Williams GJ, Gantt RW, Thorson JS (2008) The impact of enzyme engineering upon natural product glycodiversification. Curr Opin Chem Biol 12:556-564.
5. Griffith BR, Langenhan JM, Thorson JS (2005) 'Sweetening' natural products via glycorandomization. Curr Opin Biotechnol 16:622-630. (Pubitemid 41654640)
6. Blanchard S, Thorson JS (2006) Enzymatic tools for engineering natural product glycosylation. Curr Opin Chem Biol 10:263-271. (Pubitemid 43815777)
7. Lairson LL, Henrissat B, Davies GJ, Withers SG (2008) Glycosyltransferases: Structures, functions, and mechanisms. Annu Rev Biochem 77:521-555.
8. Williams GJ, Thorson JS (2009) Natural product glycosyltransferases: properties and applications. Adv Enzymol Relat Areas Mol Biol 76:55-119.
9. PalcicMM(2011) Glycosyltransferases as biocatalysts. Curr Opin Chem Biol 15:226-233.
10. Chang A, Singh S, Phillips GN, Thorson JS (2011) Glycosyltransferase structural biology and its role in the design of catalysts for glycosylation. Curr Opin Biotechnol, 10.1016/j.copbio.2011.04.013.
11. Thorson JS, et al. (2000) Understanding and exploiting nature's chemical arsenal: the past, present and future of calicheamicin research. Curr Pharm Des 6:1841-1879.
12. Ahlert J, et al. (2002) The calicheamicin gene cluster and its iterative type I enediyne PKS. Science 297:1173-1176. (Pubitemid 36193351)
13. Liu W, Christenson SD, Standage S, Shen B (2002) Biosynthesis of the enediyne antitumor antibiotic C-1027. Science 297:1170-1173. (Pubitemid 36193350)
14. Horsman GP, Chen Y, Thorson JS, Shen B (2010) Polyketide synthase chemistry does not direct biosynthetic divergence between 9- and 10-membered enediynes. Proc Natl Acad Sci USA 107:11331-11335.
15. Zhang C, et al. (2006) Exploiting the reversibility of natural product glycosyltransferase-catalyzed reactions. Science 313:1291-1294. (Pubitemid 44330953)
16. Zhang C, et al. (2008) Biochemical and structural insights of the early glycosylation steps in calicheamicin biosynthesis. Chem Biol 15:842-853.
17. Kim KH, Kwon BM, Myers AG, Rees DC (1993) Crystal structure of neocarzinostatin, an antitumor protein-chromophore complex. Science 262:1042-1046. (Pubitemid 24035040)
18. Hu Y, et al. (2003) Crystal structure of the MurG:UDP-GlcNAc complex reveals common structural principles of a superfamily of glycosyltransferases. Proc Natl Acad Sci USA 100:845-849. (Pubitemid 36183918)
19. Bolam DN, et al. (2007) The crystal structure of two macrolide glycosyltransferases provides a blueprint for host cell antibiotic immunity. Proc Natl Acad Sci USA 104:5336-5341. (Pubitemid 47175681)
20. Mulichak AM, et al. (2003) Structure of the TDP-epi- vancosaminyltransferase GtfA from the chloroeremomycin biosynthetic pathway. Proc Natl Acad Sci USA 100:9238-9243. (Pubitemid 37033913)
21. Mulichak AM, Lu W, Losey HC, Walsh CT, Garavito RM (2004) Crystal structure of vancosaminyltransferase GtfD from the vancomycin biosynthetic pathway: Interactions with acceptor and nucleotide ligands. Biochemistry 43:5170-5180. (Pubitemid 38620908)
22. OffenW, et al. (2006) Structure of a flavonoid glucosyltransferase reveals the basis for plant natural product modification. EMBO J 25:1396-1405.
23. Frey PA, Whitt SA, Tobin JB (1994) A low-barrier hydrogen bond in the catalytic triad of serine proteases. Science 264:1927-1930. (Pubitemid 24245638)
24. Cleland WW, Kreevoy MM (1994) Low-barrier hydrogen bonds and enzymic catalysis. Science 264:1887-1890. (Pubitemid 24245628)
25. Cleland WW, Frey PA, Gerlt JA (1998) The low barrier hydrogen bond in enzymatic catalysis. J Biol Chem 273:25529-25532. (Pubitemid 28475766)
26. Hoffmeister D, Ichinose K, Bechthold A (2001) Two sequence elements of glycosyltransferases involved in urdamycin biosynthesis are responsible for substrate specificity and enzymatic activity. Chem Biol 8:557-567. (Pubitemid 32532972)
27. Hoffmeister D, et al. (2002) Engineered urdamycin glycosyltransferases are broadened and altered in substrate specificity. Chem Biol 9:287-295. (Pubitemid 34253411)
28. Williams GJ, Zhang C, Thorson JS (2007) Expanding the promiscuity of a natural-product glycosyltransferase by directed evolution. Nat Chem Biol 3:657-662. (Pubitemid 47417707)
29. Cantarel BL, et al. (2009) The Carbohydrate-Active EnZymes database (CAZy): An expert resource for Glycogenomics. Nucleic Acids Res 37:D233-238.
30. Otwinowski Z, Minor W (1997) Processing of X-ray diffraction data collected in oscillation mode. Methods Enzymol 276:307-326. (Pubitemid 27085611)
31. Wang J, Kamtekar S, Berman AJ, Steitz TA (2005) Correction of X-ray intensities from single crystals containing lattice-translocation defects. Acta Crystallogr D Biol Crystallogr 61:67-74. (Pubitemid 41615532)
32. Hare S, Cherepanov P, Wang J (2009) Application of general formulas for the correction of a lattice-translocation defect in crystals of a lentiviral integrase in complex with LEDGF. Acta Crystallogr D Biol Crystallogr 65:966-973.
33. Adams PD, et al. (2010) PHENIX: A comprehensive Python-based system for macromolecular structure solution. Acta Crystallogr D Biol Crystallogr 66:213-221.
34. Sheldrick GM (2008) A short history of SHELX. Acta Crystallogr A 64:112-122.
35. delaFortelle E, Bricogne G (1997) Maximum-likelihood heavy-atom parameter refinement for multiple isomorphous replacement and multiwavelength anomalous diffraction methods. Methods Enzymol 276:472-494.
36. Cowtan KD, Main P (1996) Phase combination and cross validation in iterated density-modification calculations. Acta Crystallogr D Biol Crystallogr 52:43-48. (Pubitemid 126512681)
37. Emsley P, Cowtan K (2004) Coot: Model-building tools for molecular graphics. Acta Crystallogr D Biol Crystallogr 60:2126-2132. (Pubitemid 41742764)
38. Painter J, Merritt EA (2006) TLSMD web server for the generation of multi-group TLS models. J Appl Crystallogr 39:109-111.
39. Laskowski RA, Macarthur MW, Moss DS, Thornton JM (1993) Procheck: A program to check the stereochemical quality of protein structures. J Appl Crystallogr 26:283-291.
40. Davis IW, et al. (2007) MolProbity: All-atom contacts and structure validation for proteins and nucleic acids. Nucleic Acids Res 35:W375-383.
41. Delano WL (2002) The PyMOL Molecular Graphics System (DeLano Scientific, San Carlos, CA).