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Total synthesis of Met10-teixobactin
Affiliation:1. Organic Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pune 411008, India;2. Academy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India;1. Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt;2. Pharmacology Department, Faculty of Veterinary Medicine, Suez Canal University, Ismailia 41522, Egypt;3. Pharmacology and Toxicology Department, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt;4. Medicinal Chemistry Department, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt;1. Department of Applied Chemistry, Faculty of Science, South Tehran Branch, Islamic Azad University, P.O. Box 177761-3651, Tehran, Iran;2. Department of Chemistry, Buinzahra Branch, Islamic Azad University, P.O. Box 14115-175, Buinzahra, Iran;3. Center for Catalysis Research and Innovation, BAHERENERGY Institute of Technology, Department of Chemistry, P.O. Box 13487-55613, Tehran, Iran
Abstract:The total synthesis of cyclic depsipeptide Met10-teixobactin in solution-phase is described. Teixobactin is a structurally and mechanistically novel antimicrobial peptidic natural product with very impressive activities against Gram-positive pathogens. It happens to possess an l-allo-enduracididine (End) residue as part of macrocyclic ring which is not readily accessible. In this report, we have used serine ligation strategy as the key step to prepare an analogue of teixobactin where End being replaced with a readily available amino acid methionine.
Keywords:Teixobactin  Cyclic tetrapeptides  Serine ligation  Antibiotic
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