Synthesis, stereochemistry, and biological properties of the depigmenting agents, melanostatin, feldamycin and analogs.
Syntheses of melanostatin and feldamycin have been completed from L-serine and L-threonine, respectively, and the configuration of unknown asymmetric carbons determined. Feldamycin analogs have also been prepared and the L-tryptophyl analog was the most potent in the depigmentation of Streptomyces bikiniensis and B16 melanoma cells.
Imae
K
K
Bristol-Myers Squibb Research Institute, Tokyo, Japan.
Kamachi
H
H
Yamashita
H
H
Okita
T
T
Okuyama
S
S
Tsuno
T
T
Yamasaki
T
T
Sawada
Y
Y
Ohbayashi
M
M
Naito
T
T
D000818:Animals; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D006639:Histidine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D009075:MSH Release-Inhibiting Hormone / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology / Q000627:therapeutic use; D008543:Melanins / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D008546:Melanoma, Experimental / Q000188:drug therapy; D008968:Molecular Conformation; D012694:Serine / Q000378:metabolism; D013302:Streptomyces / Q000187:drug effects / Q000378:metabolism; D013912:Threonine / Q000378:metabolism; D014407:Tumor Cells, Cultured
D000900:Anti-Bacterial Agents; D008543:Melanins; D013912:Threonine; D012694:Serine; D006639:Histidine; C013529:feldamycin; D009075:MSH Release-Inhibiting Hormone