Glycopeptide antibiotic analogs efficient against vancomycin-resistant bacteria: a patent evaluation (WO2013022763)

Bibliography

• Bryskier A, Veyssier P. Glycopeptides and lipoglycopeptides. In: Bryskier A, editor. Antimicrobial agents. Antibacterial and antifungals. ASM press; Washington, DC; 2005. p. 880-905
   Google Scholar
• Nagarajan R. editor. Glycopeptide antibiotics. Marcel Dekker Inc, New York; 1994
   Google Scholar
• Kahne D, Leimkuhler C, Lu W, Walsh C. Glycopeptide and lipoglycopeptide antibiotics. Chem Rev 2005;105:425-48
   PubMed Web of Science ®Google Scholar
• Bugg TDH, Wright GD. Dutka-Malens et al. Molecular basis for vancomycin resistance in Enterococcus faecium BM4147: biosynthesis of a depsipeptide peptidoglycan precursor by vancomycin resistance proteins VanH and VanA. Biochemistry 1991;30:10408-15
   PubMed Web of Science ®Google Scholar
• Malabarba A in the lecture on the ICCAC-6 in 1998 6st Int. Conference on Chemistry of antibiotics and related microbial products, 30 August – 4 September 1998; Bologna, Italy
   Google Scholar
• Evans D, Wood MR, Trotter W, et al. Total synthesis of vancomycin and eremomycin aglycons. Angew Chem Int Ed 1998;37:2700-4
   PubMed Web of Science ®Google Scholar
• Evans DA, Katz J L, Peterson GS, Hintermann T. Total Synthesis of Teicoplanin Aglycon. J Am Chem Soc 2001;123:12411-13
   Google Scholar
• Evans DA, Dinsmore CJ, Watson PS, et al. Nonconventional stereochemical issues in the design of the synthesis of the vancomycin antibiotics. challenges imposed by axial and non-planar chiral elements in the heptapeptide aglycons. Angew Chem Int Engl 1998;37:2704-8
   Web of Science ®Google Scholar
• Evans DA, Wood MR, Trotter BW, et al. Total synthesis of vancomycin and eremomycin aglycons. Angew Chem Int Engl 1998;37:2700-4
   PubMed Web of Science ®Google Scholar
• Nicolaou KC, Mitchell HJ, Jain NF, et al. Total synthesis of vancomycin. Angew Chem Int Engl 1999;38:240-4
   Google Scholar
• Nicolaou KC, Boddy CNC, Brasse S, Winssinger N. Chemistry, biology, and medicine of the glycopeptide antibiotics. Angew Chem Int Ed 1999;38:2096-152
   PubMed Web of Science ®Google Scholar
• Boger DL, Miyazaki S, Kim Q, et al. Total synthesis of the vancomycin aglycon. J Am Chem Soc 1999;121:10004-11
   Web of Science ®Google Scholar
• Boger DL, Miyazaki S, Kim SH, et al. Diastereoselective total synthesis of the vancomycin aglycon with ordered atropisomer equilibrations. J Am Chem Soc 1999;121:3226-7
   Web of Science ®Google Scholar
• Boger DL. Vancomycin, teicoplanin, and ramoplanin: synthetic and mechanistic studies. Med Res Rev 2001;21:356-81
   PubMed Web of Science ®Google Scholar
• Xie J, Okano A, Pierce JG, et al. Total synthesis of [Ψ[C(=S)NH]Tpg4] vancomycin aglycon, [Ψ[C(=NH)NH]Tpg4]vancomycin aglycon, and related key compounds: reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-A-Lac binding. J Am Chem Soc 2012;134:1284-97
   PubMed Web of Science ®Google Scholar
• Crowley BM, Boger DL. Total synthesis and evaluation of [Ψ [CH2NH]Tpg4]vancomycin aglycon: reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-D-Lac binding. J Am Chem Soc 2006;128:2885-9
   PubMed Web of Science ®Google Scholar
• Boger DL; The Scripps research institute. Glycopeptide Antibiotic Analogs Efficient Against Vancomycin-Resistant Bacteria. WO2013022763
   Google Scholar
• Boger DL; The Scripps research institute. CH2NH]PG4] glycopeptide antibiotic analogs. US 20070173438;2007
   Google Scholar
• Xie J, Pierce JG, James RC, et al. A redesigned vancomycin engineered for dual D-Ala-D-Ala and D-Ala-D-Lac binding exhibits potent antimicrobial activity against vancomycin-resistant bacteria. J Am Chem Soc 2011;133:13946-9
   PubMed Web of Science ®Google Scholar
• Corey EJ, Boger DL. Benzothiazoles as carbonyl equivalents. Tetrahedron Lett 1978;19:5-8
   Google Scholar
• Okano A, James RC, Pierce JG, et al. Silver(I)-promoted conversion of thioamides to amidines: divergent synthesis of a key series of vancomycin aglycon residue 4 amidines that clarify binding behavior to model ligands. JACS 2012;134:8790-3
   Google Scholar
• Allen NE, LeTourneau DL, Hobbs JN Jr. The role of hydrophobic side chain as determinants of antibacterial activity of semisynthetic glycopeptide antibiotics. J Antibiot 1997;50:677-84
   PubMed Web of Science ®Google Scholar
• Maples KR, Wheeler C, Ip EY, et al. AN0900, a novel antibiotic under development for biodefense against anthrax. J Med Chem 2007;50:3681-5
   Google Scholar
• Plattner J, Chu D, Mirchink E, et al. N'-(alpha -Aminoacyl)- and N'-alpha-(N-alkylamino)acyl derivatives of vancomycin and eremomycin. II. Antibacterial activity of N'-(alpha-aminoacyl)- and N'- alpha -(N-alkylamino)acyl derivatives of vancomycin and eremomycin. J Antibiot 2007;60:245-50
   PubMed Web of Science ®Google Scholar
• Printsevskaya SS, Pavlov AY, Olsufyeva EN, et al. The role of the glycopeptide framework in the antibacterial activity of hydrophobic derivatives of glycopeptide antibiotics. J Med Chem 2003;46:12041-9
   Web of Science ®Google Scholar
• Coyle E, Rybak M. Activity of oritavancin (LY 333328), an investigational glycopeptide, compared to that of vancomycin against multidrug-resistant Streptococcus pneumoniae in an in vitro pharmacodynamic model. Antimicrob Agents Chemother 2001;45:706-9
   PubMed Web of Science ®Google Scholar
• Plattner JJ, Chu D, Mirchink EP, et al. N'-(alpha -Aminoacyl)- and N'- alpha -(N-Alkylamino)acyl Derivatives of Vancomycin and Eremomycin. II. Antibacterial activity of N'-(alpha -aminoacyl)- and N'- alpha -(N -alkylamino)acyl derivatives of Vancomycin and Eremomycin. J. Antibiotics 2007;60:245-50
   PubMed Web of Science ®Google Scholar
• Ashford PA, Bew SP. Recent advances in the synthesis of new glycopeptide antibiotics. Chem Soc Rev 2012;41:957-78
   Google Scholar
• Kim SJ, Matsuoka S, Patti GJ, Schaefer J. Vancomycin derivative with damaged D-Ala-D-Ala binding cleft binds to cross-linked peptidoglycan in the cell wall of Staphylococcus aureus. Biochemistry 2008;47:3822-31
   Google Scholar
• Kim SJ, Kelly SE, Tanaka KS. Locations of the hydrophobic side chains of lipoglycopeptides bound to the peptidoglycan of Staphylococcus aureus. Biochemistry 2013;52:3405-14
   Google Scholar
• Kim SJ, Cegelski L, Preobrazhenskaya M, Schaefer J. Structures of Staphylococcus aureus cell-wall complexes with vancomycin, eremomycin, and chloroeremomycin derivatives by 13C-{19F} and 15N{19F} rotational-echo double resonance. Biochemistry 2006;45:5235-50
   PubMed Web of Science ®Google Scholar