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Structural identification of a novel degradant of the antibiotic pirlimycin formed under thermal stress conditions
Author(s) -
Crow Frank W.,
Duholke Wayne K.,
Martin Gary E.,
Smith Richard F.,
Thamann Thomas J.,
Cooper Anne M.,
Hallberg John W.,
Blinn James R.,
Chidestere Constance G.
Publication year - 1999
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570360436
Subject(s) - chemistry , crystal structure , homonuclear molecule , nuclear magnetic resonance spectroscopy , fragmentation (computing) , molecule , stereochemistry , mass spectrometry , crystallography , chromatography , organic chemistry , computer science , operating system
The structure of a novel, thermally‐induced degradant of the antibiotic pirlimycin is presented. The degradant was discovered during thermal stress stability testing of pirlimycin. The structure was determined using high resolution mass spectrometry, ms/ms fragmentation, and extensive nmr studies including a combination of homonuclear TOCSY and gradient, inverse‐detected 2‐D nmr experiments which included GHSQC and GHMBC. All nmr, high resolution ms and ms/ms fragmentation data are consistent with loss of a molecule of HCl during a ring closure involving one of the hydroxyl moieties from the sugar portion of the molecule forming a tetrahydrofurano[3,2‐ b ]perhydropyran ring structure. The X‐ray crystal structure is reported for pirlimycin. Using this structure molecular modelling studies are performed which demonstrate the feasibility of the formation of the new structure.