AbstractPure 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 13C‐NMR spectra.

Isopenicillin N (I) and penicillin N (II) were separated effectively by reversed phase HPLC as derivatives of chiral 2, 3, 4, 6-tetra- O-acetyl-β-D-glucopyranosyl isothiocyanate (III). This permitted identification of isopenicillin N isolated by HPLC during a biosynthetic cell-free experiment using α-L-aminoadipyl-L-cysteinyl-D-valine (IV) as precursor.

A new cepham metabolite has been isolated from the filtered broth of Cephalosporium acremonium by high performance liquid chromatography (HPLC) and identified as 7 beta-(5-D-amino-adipamido)-3 beta-hydroxy-3 alpha-methyl-cepham-4 alpha-carboxylic acid (I). Pure penicillin N was prepared using HPLC in the analytical mode. When I was added in place of penicillin N as substrate for the cell-free biosynthetic of cephalosporin, no formation of deacetoxycephalosporin C (II) was observed. A synthetic cepham derivative, 7 beta-(5-D-aminoadipamido)-3-exomethylene-cepham-4 alpha-carboxylic acid (III) was also tested in the cell-free system as a possible intermediate. The compound III was shown to be an inhibitor of the ring expansion enzyme that converts penicillin N to deacetoxycephalosporin C.

Abstractα‐Aminoadipoyl‐alanyl‐valine, α‐aminoadipoyl‐serinyl‐valine and α‐aminoadipoyl‐serinyl‐isodehydrovaline have been isolated from the fermentation broth of P. chrysogenum. The configuration of α‐aminoadipoyl‐serinyl‐valine has been shown to be L, L, D.

Chemischer InformationsdienstVolume 8, Issue 10 Natural Products ChemInform Abstract: THE USE OF CARBON-13 NMR SPECTROSCOPY IN BIOSYNTHETIC STUDIES. II. BIOSYNTHESIS OF NARASIN, A NEW POLYETHER IONOPHORE FROM FERMENTATION OF STREPTOMYCES AUREOFACIENS D. E. DORMAN, D. E. DORMANSearch for more papers by this authorJ. W. PASCHAL, J. W. PASCHALSearch for more papers by this authorW. M. NAKATSUKASA, W. M. NAKATSUKASASearch for more papers by this authorL. L. HUCKSTEP, L. L. HUCKSTEPSearch for more papers by this authorN. NEUSS, N. NEUSSSearch for more papers by this author D. E. DORMAN, D. E. DORMANSearch for more papers by this authorJ. W. PASCHAL, J. W. PASCHALSearch for more papers by this authorW. M. NAKATSUKASA, W. M. NAKATSUKASASearch for more papers by this authorL. L. HUCKSTEP, L. L. HUCKSTEPSearch for more papers by this authorN. NEUSS, N. NEUSSSearch for more papers by this author First published: March 8, 1977 https://doi.org/10.1002/chin.197710375Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume8, Issue10March 8, 1977 RelatedInformation

AbstractThe labeling of the polyether ionophore, narasin, using 13C‐labeled acetate, propionates, and butyrates in the course of fermentation of Streptomyces aureofacies resulted in the isolation of differently labeled compounds. A careful examination of the 13C‐NMR. spectral data indicated derivation of narasin from five acetate, seven propionate, and three butyrate units. The evidence of indirect incorporation of 13C led to the first documented demonstration of conversion of propionate to butyrate in the course of the synthesis of narasin by S. aureofaciens.

Auf Grund spektroskopischer Untersuchungen konnte die Struktur eines neuen Alkaloids ausVinca rosea L. als Desacetoxy-VLB aufgeklärt werden.

AbstractBei der Behandlung der Titelverbindung (I) mit verschiedenen Streptomyces‐Arten wird der Äther (II) bzw. das Hydroxy‐Derivat (III) gebildet.

The conversion of vindoline (II) using S. albogriseolus led to the isolation of several compounds including des-Na-methyl vindoline (III) in 8–10% yield.

AbstractVindoline, a major alkaloid from Vinca rosea L was subjected to microbiological conversion using Streptomyces cultures.Several new metabolites were isolated and their structures elucidated.

Die mikrobiologische Demethylierung von Vindolin (I) liefert als Hauptprodukt die Titelverbindung (II) in 8‐10%iger Ausbeute.

AbstractThe conversion of VLB using different Streptomycetes led to the isolation of VLB‐ether (3) and Hydroxy VLB (6). The structural assignments have been made by NMR. and high resolution mass spectral data.

AbstractDie aus dem deuterierten Brompropan (I) über den Malonester (III) synthetisierte Bromisovaleriansäure (V) gibt mit Ammoniak das deuterierte D,L‐Valin (VI).

AbstractDie mikrobiologische Demethylierung von Vindolin (I) liefert als Hauptprodukt die Titelverbindung (II) in 8‐10%iger Ausbeute.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTAdditions and Corrections - Use of Chiral Isopropyl Groups in Biosynthesis. Synthesis of (2RS,3S)·[4-13C]ValineJ. E. Baldwin, J. Löliger, W. Rastetter, N. Neuss, L. L. Huckstep, and N. De La HigueraCite this: J. Am. Chem. Soc. 1973, 95, 19, 6511–6512Publication Date (Print):September 1, 1973Publication History Published online28 January 2004Published inissue 1 September 1973https://pubs.acs.org/doi/10.1021/ja00800a612https://doi.org/10.1021/ja00800a612research-articleACS PublicationsRequest reuse permissionsArticle Views22Altmetric-Citations1LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts

AbstractDurch Carboxylierung von 2‐Phenyl‐cyclopropyl‐MgBr mit "CO2 bei ‐60°C und aufeinanderfolgende Veresterung (mit CH2N2), Äquilibrierung des gebildeten Esters zu seinem trans‐Isomeren (mit K‐tert.‐butylat/tert.‐Butanol) und Hydrolyse mit KOH in Methanol unter Rückflußkochen wird trans‐2‐Phenylcyclopropan‐carbonsäure (85% Ausbeute) dargestellt, die an der Carboxyfunktion mit 13C markiert ist.