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 | Zendy

Kukolja S. | Zendy; Miller R. D. | Zendy; Duckworth D. C. | Zendy; Dorman D. E. | Zendy; Huckstep L. L. | Zendy; Neuss Norbert | Zendy; Quenner S. W. | Zendy

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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.

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