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RECENT PUBLICATIONS AND PATENTS Drawz, S. M.; Bethel, C. R.; Doppalapudi, V. R.; Sheri, A.; Pagadala, S. R. R.; Hujer, A. M.; Skalweit, M. J.; Andersen, V. E.; Chen, S. G.; Buynak, J. D.; Bonomo, R. A. Penicillin Sulfone Inhibitors of the Class D b-lactamases. Antimicrob. Agents Chemother. 2010, in press. Buynak, J. D.; Sheri, A.; Pagadala, S.R.R. Preparation and antibacterial activity of .beta.-lactamase inhibitory compounds. U.S. Pat. Appl. Publ. (2010), 104 pp. US 2010009954 A1 20100114 Ganta, S. R.; Perumal, S.; Pagadala, S. R. R.; Samuelsen, O.; Spencer, J.; Pratt, R. F.; Buynak, J. D. Approaches to the simultaneous inactivation of metallo- and serine-β-lactamases, Bioorg. Med. Chem. Lett. 2009, 19: 1618-1622. Kalp, M.; Totir, M. A.; Buynak, J. D.; Carey, P. R. Different intermediate populations formed by tazobactam, sulbactam, and clavulanate reacting with SHV-1 β-lactamases: Raman crystallographic evidence. J. Am. Chem. Soc. 2009, 131: 2338-2347. Pattanaik, P.; Bethel, C. R.; Hujer, A. M.; Hujer, K. M.; Distler, A. M.; Taracila, M.; Anderson, V. E.; Fritsche, T. R.; Jones, R. N.; Pagadala, S. R. R.; van den Akker, F.; Buynak, J. D.; Bonomo, R. A. Strategic Design of an Effective β-Lactamase Inhibitor: LN-1-255, A 6-alkylidene--2'-substituted penicillin sulfone. J. Biol. Chem. 2009, 284: 945-953. Totir, M. A.; Cha, J.; Ishiwata, A.; Wang, B.; Sheri, A.; Anderson, V. E.; Buynak, J.; Mobashery, S.; Carey, P. R. Why Clinically Used Tazobactam and Sulbactam Are Poor Inhibitors of OXA-10 β-Lactamase: Raman Crystallographic Evidence. Biochemistry 2008, 47: 4094-4101. Buynak, J. D.. Cutting and Stitching: The Cross-Linking of Peptidoglycan in the Assembly of the Bacterial Cell Wall. ACS Chem. Biol. 2007, 2: 602-605. Kalp, M.; Sheri, A.; Buynak, J. D.; Bethel, C. R.; Bonomo, R. A.; Carey, P. R. Efficient Inhibition of Class A and Class D β-Lactamases by Michaelis Complexes. J. Biol. Chem. 2007, 282: 21588-21591. Totir, M. A.; Helfand, M. S.; Carey, M. P.; Sheri, A.; Buynak, J. D.; Bonomo, R. A.; Carey, P. R. Sulbactam Forms Only Minimal Amounts of Irreversible Acrylate-Enzyme with SHV-1 β-Lactamase. Biochemistry 2007, 46: 8980-8987. Helfand, M. S.; Taracila, M. A.; Totir, M. A.; Bonomo, R. A.; Buynak, J. D.; van den Akker, F.; Carey, P. R. Raman Crystallographic Studies of the Intermediates Formed by Ser130Gly SHV, a β-Lactamase that Confers Resistance to Clinical Inhibitors. Biochemistry 2007, 46: 8689-8699. Padayatti, P. S.; Sheri, A.; Totir, M. A.; Helfand, M. S.; Carey, M. P.; Anderson, V. E.; Carey, P. R.; Bethel, C. R.; Bonomo, R. A.; Buynak, J. D.; van den Akker, F. Rational Design of a β-Lactamase Inhibitor Achieved via Stabilization of the trans-Enamine Intermediate: 1.28 .ANG. Crystal Structure of wt SHV-1 Complex with a Penam Sulfone. J. Am. Chem. Soc. 2006, 128: 13235-13242. Buynak, J. D.; Chen, H.. Cephalosporin-derived mercaptans as inhibitors of serine and metallo-β-lactamases. U.S. Pat. Appl. Publ. (2006), WO 2003087105 A1 20031023 17pp. Zhu, D.; Yang, Y.; Buynak, J. D.; Hua, L.. Stereoselective ketone reduction by a carbonyl reductase from Sporobolomyces salmonicolor. Substrate specificity, enantioselectivity and enzyme-substrate docking studies. Org. Biomol. Chem. 2006, 4: 2690-2695. Buynak, John D.. Understanding the longevity of the β-lactam antibiotics and of antibiotic/ β-lactamase inhibitor combinations. Biochem. Pharmacol. 2006, 71: 930-940. Sulton, D.; Pagan-Rodriguez, D.; Zhou, X.; Liu, Y.; Hujer, A. M.; Bethel, C. R.; Helfand, Marion S.; Thomson, Jodi M.; Anderson, Vernon E.; Buynak, John D.; Ng, Lily M.; Bonomo, Robert A. Clavulanic Acid Inactivation of SHV-1 and the Inhibitor-resistant S130G SHV-1 β-Lactamase: Insights into the mechanism of inhibition. J. Biol. Chem. 2005, 280: 35528-35536. Black, J. A.; Thomson, K. S.; Buynak, J. D.; Pitout, J. D. D. Evaluation of β-lactamase inhibitors in disk tests for detection of plasmid-mediated AmpC β-lactamases in well-characterized clinical strains of Klebsiella spp. J. Clin. Microbiol. 2005, 43: 4168-4171. Buynak, J. D.; Ghadachanda, V. Rao; Vogeti, L.; Zhang, H.; Chen, H.. Synthesis and Evaluation of 3-(Carboxymethylidene)- and 3-(Carboxymethyl)penicillinates as Inhibitors of β-Lactamase. J. Org. Chem. 2005, 70: 4510-4513. Hujer, A. M.; Kania, M.; Gerken, T.; Anderson, V. E.; Buynak, J. D.; Ge, X.; Caspers, P.; Page, M. G. P.; Rice, L. B.; Bonomo, R. A. Structure-activity relationships of different β-lactam antibiotics against a soluble form of Enterococcus faecium PBP5, a type II bacterial transpeptidase. Antimicrob. Agents Chemother., 2005, 49: 612-618. Buynak, J. D.. The discovery and development of modified penicillin- and cephalosporin-derived β-lactamase inhibitors. Curr. Med. Chem. 2004, 11: 1951-1964. Buynak, J. D.; Chen, H.; Vogeti, L.; Gadhachanda, V. R.; Buchanan, C. A.; Palzkill, T.; Shaw, Robert W.; Spencer, James; Walsh, Timothy R. Penicillin-derived inhibitors that simultaneously target both metallo- and serine-β-lactamases. Bioorg. Med. Chem. Lett. 2004, 14: 1299-1304. Beharry, Z.; Chen, H.; Gadhachanda, V. R.; Buynak, J.D.; Palzkill, T. Evaluation of penicillin-based inhibitors of the class A and B β-lactamases from Bacillus anthracis. Biochem. Biophys. Res. Commun. 2004, 313: 541-545. Buynak, J. D.; Vogeti, L. Preparation of 7-alkylidene-3-substituted-3-cephem-4-carboxylates as β -lactamase inhibitors. PCT Int. Appl. 2003, 50 pp. WO 2003020732 A2 20030313Buynak, J. D.; Chen, H. Preparation of penicillin derivatives as inhibitors of serine and metallo- β-lactamases. PCT Int. Appl. 2003, 48 pp. WO 2003087105 A1 20031023Buynak, John D.; Vogeti, Lakshminarayana; Doppalapudi, Venkata Ramana; Solomon, George Martin; Chen, Hansong. Cephalosporin-derived inhibitors of β-Lactamase. Part 4: The C3 substituent. Bioorg. Med. Chem. Lett. 2002, 12: 1663-1666. Buynak, J. D.; Vogeti, L.; Chen, H. Coupling Reactions of Cephalosporin Sulfones: A Stable 3-Stannylated Cephem. Org. Lett. 2001, 3: 2953-2956. Crichlow, G. V.; Nukaga, M.; Doppalapudi, V. R.; Buynak, J. D.; Knox, J. R. Inhibition of class C β-lactamases: Structure of a reaction intermediate with a cephem sulfone. Biochemistry 2001, 40: 6233-6239. Buynak, J. D.; Rao, A. S.; Adam, G. C.; Nidamarthy, S. D.; Doppalapudi, V. R. Synthesis, antibacterial activity and formulations of β-lactamase inhibiting cephalosporins. PCT Int. Appl. (2000), 65 pp. WO 2000063213 A1 20001026 Buynak, J. D.; Doppalapudi, V. R.; Frotan, M.; Kumar, R.; Chambers, A. Catalytic approaches to the synthesis of β-lactamase inhibitors. Tetrahedron 2000, 56: 5709-5718.Buynak, J. D.; Doppalapudi, V. R.; Adam, G. The synthesis and evaluation of 3-substituted-7-(alkylidene)cephalosporin sulfones as β-lactamase inhibitors. Bioorg. Med. Chem. Lett. 2000, 10: 853-857.Buynak, J. D.; Rao, A. S.; Doppalapudi, V. R.; Adam, G.; Petersen, P. J.; Nidamarthy, S. D. The synthesis and evaluation of 6-alkylidene-2' β-substituted penam sulfones as β-lactamase inhibitors. Bioorg. Med. Chem. Lett. 1999, 9: 1997-2002.Buynak, J. D.; Rao, A. S. Preparation of 2- β-substituted-6-alkylidenepenicillanic acid derivatives as β-lactamase inhibitors. PCT Int. Appl. (1999), 67 pp. WO 9933838 A1 19990708Buynak, J. D.; Rao, A. S.; Adam, G.; Nidamarthy, S. D.; Zhang, H. Synthesis of the First 2',6 Bridged Penams. J. Am. Chem. Soc. 1998, 120: 6846-6847.
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