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YM-24074, a new peptide antibiotic. II. Structural elucidation
T Sato1, Y Takebayashi, T Tokunaga
1Analytical Science Research Laboratories, Yamanouchi Pharmaceutical Co., Ltd., Shizuoka Prefecture, Japan.
The Journal of Antibiotics
|August 1, 1996
Summary
A new antibiotic, YM-24074, also inhibits type I collagenase. Its complex chemical structure was determined, revealing specific stereochemistry at two chiral centers.
Area of Science:
- Biochemistry
- Organic Chemistry
- Pharmacology
Background:
- Type I collagenase is implicated in various physiological and pathological processes.
- The development of novel inhibitors for collagenase is of therapeutic interest.
Purpose of the Study:
- To elucidate the structure and stereochemistry of a new antibiotic compound, YM-24074.
- To identify YM-24074 as a type I collagenase inhibitor.
Main Methods:
- Spectroscopic analysis was employed to determine the compound's structure.
- Acid degradation was used to confirm the structure and analyze stereochemistry.
- Chiral center determination was performed using degradation products.
Main Results:
- The chemical structure of YM-24074 was elucidated as N-(1"-acetyl-3"-methylbutyl)-2-[2'-[(N-hydroxycarbamoyl)methyl]heptanoyl]-hexahydropyridazine-3-carboxamide.
- The stereochemistry of two of the three chiral centers was determined to be 3S and 2'R.
Conclusions:
- YM-24074 is a novel antibiotic with type I collagenase inhibitory activity.
- The detailed structural and stereochemical information provides a basis for further pharmacological studies.