Cyclic homopentapeptides 2. Synthetic modifications of viomycin

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 9, 1997, Pages 1145-1148

  Lyssikatos, J P ^a   Chang, S P ^a   Clancy, J ^a   Dirlam, J P ^a   Finegan, S M ^a   Girard, A E ^a   Hayashi, S F ^a   Larson, D P ^a   Lee, A S ^a   Linde II, R G ^a   MacLelland, C P ^a   Petitpas, J W ^a   Seibel, S B ^a   Vu, C B ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; PENTAPEPTIDE; VANCOMYCIN; VIOMYCIN;

ANTIBACTERIAL ACTIVITY; ARTICLE; DRUG RESISTANCE; DRUG SYNTHESIS; ESCHERICHIA COLI; IN VITRO STUDY; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; PASTEURELLA MULTOCIDA; STAPHYLOCOCCUS AUREUS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 17544398657     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00187-X     Document Type: Article

References (3)

1. Dirlam, J. P.; Belton, A. M.; Birsner, N. C.; Brooks, R. R.; Chang, S.-P.; Chandrasekaran, R. Y.; Clancy, J.; Cronin, B. J.; Dirlam, B. P.; Finegan, S. M.; Froshauer, S. A.; Girard, A. E.; Hayashi, S. F.; Howe, R. J.; Kane, J. C.; Kamicker, B. J.; Kaufman, S. A.; Kolosko, N. L.; LeMay, M. A.; Linde II, R. G.; Lyssikatos, J. P.; MacLelland, C. P.; Magee, T. V.; Massa, M. A.; Miller, S. A.; Minich, M. L.; Perry, D. A.; Petitpas, J. W.; Reese, C. P.; Seibel, S. B.; Su, W.-G.; Sweeney, K. T.; Whipple, D. A.; Yang, B. V. Bioorg. Med. Chem. Lett, proceeding paper in this series.
2. Kitagawa, T.; Miura, T.; Tanaka, S.; Taniyama, H. J. Antibiotics 1973, 26, 528.
3. Typical procedures using benzylcarbamates are as follows: A solution containing 500 mg of viomycin sulfate (0.547 mmol) in 5 mL of anhydrous TFA was stirred at room temperature under an atmosphere of dry nitrogen. An excess of 4-chloro-2-fluorobenzyl carbamate (1.10 g, 5.47 mMol) was added and the resulting reaction mixture was stirred at ambient temperature for 15 h. The reaction mixture was then diluted with 50 mL of water and 12 ml of 6 N hydrochloric acid. The aqueous layer was washed 6 times with 15 mL of ethyl acetate and then poured into 30 grams of activated Diaion HP-21 resin (Mitsubishi Kasei Corp.; a high porous polymer absorption resin that was activated by soaking in methanol for 45 min and then thoroughly washing with water). The resulting reaction mixture was shaken at ambient temperature for 45 min and then filtered. The HP-21 resin was thoroughly washed with 300 mL of water and transferred to a beaker containing 250 mL of methanol. The methanol mixture was shaken at ambient temperature for 45 min and then filtered. The filtrate was concentrated under reduced pressure to give 220 mg of the product as the tri-hydrochloride salt.