References of Pepstatin (3S,4S)-3-Hydroxy-4-[[(2S)-2-[[(3S,4S)-3-hydroxy-6-methyl-4-[[(2S)-3-methyl-2-[[(2S)-3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoyl]amino]-6-methylheptanoic acid Pepstatin (3S,4S)-3-Hydroxy-4-[[(2S)-2-[[(3S,4S)-3-hydroxy-6-methyl-4-[[(2S)-3-methyl-2-[[(2S)-3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoyl]amino]-6-methylheptanoic acid Pepstatin (3S,4S)-3-Hydroxy-4-[[(2S)-2-[[(3S,4S)-3-hydroxy-6-methyl-4-[[(2S)-3-methyl-2-[[(2S)-3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoyl]amino]-6-methylheptanoic acidPepstatin
Title: Pepstatin
CAS Registry Number: 26305-03-3
CAS Name: N-(3-methyl-1-oxobutyl)-L-valyl-L-valyl-(3
S,4
S)-4-amino-3-hydroxy-6-methylheptanoyl-
N-[(1
S)-1-[(1
S)-2-carboxy-1-hydroxyethyl]-3-methylbutyl]-L-alaninamide
Synonyms: Pepstatin A;
N-isovaleryl-L-valyl-L-valyl-3-hydroxy-6-methyl-g-aminoheptanoyl-L-alanyl-3-hydroxy-6-methyl-g-aminoheptanoic acid
Molecular Formula: C34H63N5O9
Molecular Weight: 685.89
Percent Composition: C 59.54%, H 9.26%, N 10.21%, O 20.99%
Literature References: A pentapeptide pepsin inhibitor, isolated from cultured broths of
Streptomyces testaceus Hamada
et Okami and
Streptomyces argenteolus var.
toyonakensis: H. Umezawa
et al., J. Antibiot. 23, 259 (1970). Prepn: H. Umezawa
et al., DE 2028403 (1971 to Microbiochemical Res. Found.),
C.A. 74, 75201c (1971). Structure: H. Morishima
et al., J. Antibiot. 23, 263 (1970). Synthesis: H. Morishima
et al., ibid. 25, 551 (1972). Biological properties: T. Aoyagi
et al., ibid. 24, 687 (1971).
N-n-Caproyl and
N-iso-caproyl derivatives,
pepstatin B and
pepstatin C, also isolated from pepstatin-producing
Streptomyces, as minor components of crude preparations: T. Miyano
et al., ibid. 25, 489 (1972). Mechanism of pepsin inhibition: S. Kunimoto
et al., ibid. 251;
27, 413 (1974); J. Marciniszyn
et al., Adv. Exp. Med. Biol. 95, 199 (1977); D. H. Rich, E. T. O. Sun,
Biochem. Pharmacol. 29, 2205 (1980); of other acid protease inhibition: D. H. Rich
et al., Biochemistry 24, 3165 (1985). Tissue distribution in rats: D. A. W. Grant
et al., Biochem. Pharmacol. 31, 2302 (1982). Effect on gastric ulcers in man: O. Bonnevie
et al., Gut 20, 624 (1979); L. B. Svendsen
et al., Scand. J. Gastroenterol. 14, 929 (1979).
Properties: Colorless needles, mp 228-229° (dec). [a]D27 -90.3° (c = 0.288 in methanol). Sol in methanol, ethanol, acetic acid DMSO. Practically insol in benzene, chloroform, ether, and water. LD50 in mice, rats, rabbits, dogs (mg/kg): 1090, 875, 820, 450 i.p.; all >2000 orally (Umezawa, 1970).
Melting point: mp 228-229° (dec)
Optical Rotation: [a]D27 -90.3° (c = 0.288 in methanol)
Toxicity data: LD50 in mice, rats, rabbits, dogs (mg/kg): 1090, 875, 820, 450 i.p.; all >2000 orally (Umezawa, 1970)
![CAS No:26305-03-3 Pepstatin (3S,4S)-3-Hydroxy-4-[[(2S)-2-[[(3S,4S)-3-hydroxy-6-methyl-4-[[(2S)-3-methyl-2-[[(2S)-3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoyl]amino]-6-methylheptanoic acid Pepstatin (3S,4S)-3-Hydroxy-4-[[(2S)-2-[[(3S,4S)-3-hydroxy-6-methyl-4-[[(2S)-3-methyl-2-[[(2S)-3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoyl]amino]-6-methylheptanoic acid Pepstatin (3S,4S)-3-Hydroxy-4-[[(2S)-2-[[(3S,4S)-3-hydroxy-6-methyl-4-[[(2S)-3-methyl-2-[[(2S)-3-methyl-2-(3-methylbutanoylamino)butanoyl]amino]butanoyl]amino]heptanoyl]amino]propanoyl]amino]-6-methylheptanoic acidPepstatin](/structure/cas-263/26305-03-3.png)
