Isopenicillin N Synthase Binds δ-(L-α-Aminoadipoyl)-L-Cysteinyl-D-Thia-allo-Isoleucine through both Sulfur Atoms

ChemBioChem

Volumn 12, Issue 12, 2011, Pages 1881-1885

  Clifton, Ian J ^a   Ge, Wei ^a   Adlington, Robert M ^a   Baldwin, Jack E ^a   Rutledge, Peter J ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF SYDNEY   (Australia)

Author keywords

Antibiotics; Biosynthesis; Enzyme mechanisms; Metalloenzymes; Non heme iron oxidase; Penicillin

Indexed keywords

CYSTEINE DERIVATIVE; DELTA (ALPHA AMINOADIPOYL)CYSTEINYL DEXTRO THIA ALLO ISOLEUCINE; ISOLEUCINE; ISOPENICILLIN N SYNTHETASE; OXYGEN; SULFIDE; SULFUR; UNCLASSIFIED DRUG; VALINE;

ARTICLE; BINDING SITE; BIOTRANSFORMATION; COMPLEX FORMATION; CRYSTAL STRUCTURE; CRYSTALLIZATION; ENZYME BINDING; ENZYME MECHANISM; ENZYME SUBSTRATE; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

BINDING SITES; BIOCHEMISTRY; CRYSTALLOGRAPHY, X-RAY; FUNGAL PROTEINS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; IRON; ISOLEUCINE; MODELS, MOLECULAR; OLIGOPEPTIDES; OXIDATION-REDUCTION; OXIDOREDUCTASES; OXYGEN; PENICILLINS; PROTEIN BINDING; SUBSTRATE SPECIFICITY; SULFUR; VALINE;

THIA;

EID: 79961122186     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201100149     Document Type: Article

References (39)

1. J. E. Baldwin, C. J. Schofield in The Chemistry of β-Lactams (Ed.: M. I. Page), Blackie, Glasgow, 1992, p. 1.
2. M. Costas, M. P. Mehn, M. P. Jensen, L. Que, Chem. Rev. 2004, 104, 939.
3. P. C. A. Bruijnincx, G. van Koten, R. Gebbink, Chem. Soc. Rev. 2008, 37, 2716.
4. J. E. Baldwin in Special Publication No. 52 (Eds.: A. G. Brown, S. M. Roberts), The Royal Society of Chemistry, London, 1985, p. 62.
5. N. I. Burzlaff, P. J. Rutledge, I. J. Clifton, C. M. H. Hensgens, M. Pickford, R. M. Adlington, P. L. Roach, J. E. Baldwin, Nature 1999, 401, 721.
6. J. E. Baldwin, M. Bradley, Chem. Rev. 1990, 90, 1079.
7. R. D. G. Cooper, Bioorg. Med. Chem. 1993, 1, 1.
8. P. L. Roach, I. J. Clifton, V. Fulop, K. Harlos, G. J. Barton, J. Hajdu, I. Andersson, C. J. Schofield, J. E. Baldwin, Nature 1995, 375, 700.
9. P. L. Roach, I. J. Clifton, C. M. H. Hensgens, N. Shibata, C. J. Schofield, J. Hadju, J. E. Baldwin, Nature 1997, 387, 827.
10. G. Bahadur, J. E. Baldwin, L. D. Field, E.-M. M. Lehtonen, J. J. Usher, C. A. Vallejo, E. P. Abraham, R. L. White, J. Chem. Soc. Chem. Commun. 1981, 917.
11. G. A. Bahadur, J. E. Baldwin, J. J. Usher, E. P. Abraham, G. S. Jayatilake, R. L. White, J. Am. Chem. Soc. 1981, 103, 7650.
12. J. E. Baldwin, R. M. Adlington, N. J. Turner, B. P. Domayne-Hayman, H.-H. Ting, A. E. Derome, J. A. Murphy, J. Chem. Soc. Chem. Commun. 1984, 1167.
13. J. L. Morell, P. Fleckenstein, E. Gross, J. Org. Chem. 1977, 42, 355.
14. S. Wolfe, M. G. Jokinen, Can. J. Chem. 1979, 57, 1388.
15. J. M. Elkins, P. J. Rutledge, N. I. Burzlaff, I. J. Clifton, R. M. Adlington, P. L. Roach, J. E. Baldwin, Org. Biomol. Chem. 2003, 1, 1455.
16. M. Bodanzky, A. Bodanzky in Reactivity and Structure Concepts in Organic Chemistry, Vol. 21 (Eds.: K. Hafner, C. W. Rees, B. M. Trost, J.-M. Lehn, P. v. R. Schleyer, R. Zahruchik), Springer, Berlin, 1984, p. 172.
17. P. L. Roach, I. J. Clifton, C. M. H. Hensgens, N. Shibata, A. J. Long, R. W. Strange, S. S. Hasnain, C. J. Schofield, J. E. Baldwin, J. Hajdu, Eur. J. Biochem. 1996, 242, 736.
18. P. J. Rutledge, N. I. Burzlaff, J. M. Elkins, M. Pickford, J. E. Baldwin, P. L. Roach, Anal. Biochem. 2002, 308, 265.
19. J. M. Ogle, I. J. Clifton, P. J. Rutledge, J. M. Elkins, N. I. Burzlaff, R. M. Adlington, P. L. Roach, J. E. Baldwin, Chem. Biol. 2001, 8, 1231.
20. A. R. Grummitt, P. J. Rutledge, I. J. Clifton, J. E. Baldwin, Biochem. J. 2004, 382, 659.
21. A. Daruzzaman, I. J. Clifton, R. M. Adlington, J. E. Baldwin, P. J. Rutledge, ChemBioChem 2006, 7, 351.
22. A. C. Stewart, I. J. Clifton, R. M. Adlington, J. E. Baldwin, P. J. Rutledge, ChemBioChem 2007, 8, 2003.
23. A. R. Howard-Jones, J. M. Elkins, I. J. Clifton, P. L. Roach, R. M. Adlington, J. E. Baldwin, P. J. Rutledge, Biochemistry 2007, 46, 4755.
24. W. Ge, I. J. Clifton, A. R. Howard-Jones, J. E. Stok, R. M. Adlington, J. E. Baldwin, P. J. Rutledge, ChemBioChem 2009, 10, 2025.
25. E. L. Hegg, L. Que Jr., Eur. J. Bioch. 1997, 250, 625.
26. W. Ge, I. J. Clifton, J. E. Stok, R. M. Adlington, J. E. Baldwin, P. J. Rutledge, J. Am. Chem. Soc. 2008, 130, 10096.
27. A. J. Long, I. J. Clifton, P. L. Roach, J. E. Baldwin, C. J. Schofield, P. J. Rutledge, Biochem. J. 2003, 372, 687.
28. A. J. Long, I. J. Clifton, P. L. Roach, J. E. Baldwin, P. J. Rutledge, C. J. Schofield, Biochemistry 2005, 44, 6619.
29. A. R. Howard-Jones, P. J. Rutledge, I. J. Clifton, R. M. Adlington, J. E. Baldwin, Biochem. Biophys. Res. Commun. 2005, 336, 702.
30. W. Ge, I. J. Clifton, J. E. Stok, R. M. Adlington, J. E. Baldwin, P. J. Rutledge, Org. Biomol. Chem. 2010, 8, 122.
31. W. Ge, I. J. Clifton, J. E. Stok, R. M. Adlington, J. E. Baldwin, P. J. Rutledge, Biochem. Biophys. Res. Commun. 2010, 398, 659.
32. J. C. Sheehan, J. Preston, P. A. Cruickshank, J. Am. Chem. Soc. 1965, 87, 2492.
33. Z. Otwinowski, W. Minor, Methods Enzymol. 1997, 276, 307.
34. Collaborative Crystallography Project Number 4, Acta Crystallogr. Sect. D Biol. Crystallogr. 1994, 50, 760.
35. G. N. Murshudov, A. A. Vagin, E. J. Dodson, Acta Crystallogr. Sect. D Biol. Crystallogr. 1997, 53, 240.
36. P. Emsley, K. Cowtan, Acta Crystallogr. Sect. D Biol. Crystallogr. 2004, 60, 2126.
37. L. Potterton, S. McNicholas, E. Krissinel, J. Gruber, K. Cowtan, P. Emsley, G. N. Murshudov, S. Cohen, A. Perrakis, M. Noble, Acta Crystallogr. Sect. D Biol. Crystallogr. 2004, 60, 2288.
38. K. Diederichs, P. A. Karplus, Nat. Struct. Biol. 1997, 4, 269.
39. M. S. Weiss, J. Appl. Crystallogr. 2001, 34, 130.