Diastereoselective synthesis of all stereoisomers of beta-methoxytyrosine, a component of papuamides.
beta-Methoxytyrosine (beta-OMeTyr) is a stereoundefined component of papuamides A and B, novel cyclodepsipeptides, with anti-HIV and cytotoxic activities. For structural determination and total synthesis of papuamides, all stereoisomers of beta-OMeTyr were stereoselectively prepared from (S)- and (R)-serine, respectively.
Okamoto
Naoki
N
Graduate School of Pharmaceutical Sciences, Chiba University, Yayoi-cho, Inage-ku, Chiba 263-8522, Japan.
Hara
Osamu
O
Makino
Kazuishi
K
Hamada
Yasumasa
Y
D000818:Animals; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D020650:Combinatorial Chemistry Techniques; D047630:Depsipeptides; D008781:Methyltyrosines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010219:Papua New Guinea; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry; D012694:Serine / Q000737:chemistry; D017550:Spectroscopy, Fourier Transform Infrared; D013237:Stereoisomerism
D019380:Anti-HIV Agents; D000970:Antineoplastic Agents; D047630:Depsipeptides; D008781:Methyltyrosines; D010456:Peptides, Cyclic; C474170:papuamide A; C474171:papuamide B; D012694:Serine