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High performance liquid chromatography (HPLC) of natural products part VI. Sulfoxides of penicillin N and cephalosporin c and their role in biosynthesis of β‐lactam antibiotics
Author(s) -
Kukolja S.,
Miller R. D.,
Duckworth D. C.,
Dorman D. E.,
Huckstep L. L.,
Neuss Norbert,
Quenner S. W.
Publication year - 1984
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19840670329
Subject(s) - chemistry , sulfoxide , penicillin , cephalosporin , cephalosporin c , high performance liquid chromatography , cephalosporin antibiotic , lactam , chromatography , dimethyl sulfoxide , antibiotics , organic chemistry , stereochemistry , biochemistry
Pure pencillin N α‐sulfoxide ( 1 ) and penicillin N β‐sulfoxide ( 2 ) were obtained by HPLC and tested as substrates for deacetoxycephalosporin C synthetase (DXCS). Neither one of the sulfoxides was utilized under conditions of conversion of penicillin N ( 8 ) to deacetoxycephalosporin C ( 9 ). The cephalosporin C α and β‐sulfoxides ( 3 and 4 , resp.) were also prepared. Relative stabilities of the sulfoxides 3 and 4 are discussed by interpretation of the 13 C‐NMR spectra.