Pyrostatins A and B, new inhibitors of N-acetyl-beta-D-glucosaminidase, produced by Streptomyces sp. SA-3501.
Pyrostatins A and B, new inhibitors of N-acetyl-beta-D-glucosaminidase (GlcNAc-ase), have been purified from the culture broth of Streptomyces sp. SA-3501 isolated from a marine environment. They were purified by chromatography on Dowex 50W, silica gel and Capcell Pak C18 (HPLC) followed treatment with active carbon and then isolated as white powders. The structures of pyrostatins A and B were determined by NMR studies to be 4-hydroxy-2-imino-1-methylpyrrolidine-5-carboxylic acid and 2-imino-1-methylpyrrolidine-5-carboxylic acid, respectively. They were competitive with the substrate, and the inhibition constants (Ki) of pyrostatins A and B were 1.7 x 10(-6) M and 2.0 x 10(-6) M respectively.
Aoyama
T
T
Institute of Microbial Chemistry, Tokyo, Japan.
Kojima
F
F
Imada
C
C
Muraoka
Y
Y
Naganawa
H
H
Okami
Y
Y
Takeuchi
T
T
Aoyagi
T
T
D000118:Acetylglucosaminidase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D002853:Chromatography, Liquid; D004305:Dose-Response Relationship, Drug; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D007097:Imines / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008970:Molecular Weight; D011759:Pyrrolidines / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology*; D012995:Solubility; D013302:Streptomyces / Q000145:classification / Q000378:metabolism*; D013997:Time Factors
D007097:Imines; D011759:Pyrrolidines; C094715:pyrostatin B; C094714:pyrostatin A; D006026:Glycoside Hydrolases; D000118:Acetylglucosaminidase