Ein neues Verfahren zur Herstellung von 19-Norsteroiden

Summary The new methods for the production of 19-norsteroids described involve the conversion of 5-halogen-6-hydroxy-steroids into the corresponding 5-halogen-6:19-ethers either with lead tetraacetate or by the hypoiodite reaction^8,10. The 6:19-oxygen bridge is then opened reductively either directly or after oxidation of the 6:19-ethers to lactones or preferably after introduction of a ^4,6-3-oxo grouping. Acylolytic cleavage of the ⁴-3-oxo-6:19-ethers followed by alkaline hydrolysis gives ^4,6-3-oxo-19-hydroxy-steroids. The 19-hydroxycompounds formed are easily converted into 19-norsteroids by known methods.

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Über Steroide, 189. (vorläufige) Mitteilung; 188. Mitt. vgl.J. Kalvoda, J. Schmidlin, G. Anner undA. Wettstein, Exper.18, 398 (1962).     

Synthese von Solanidin aus Demissidin

Summary The steroidal alkaloid solanidine (solanid-5-ene-3-ol, II) which occurs in the potato plantSolanum tuberosum L. has been synthesized from demissidine (5-solanidane-3-ol, I), an alkaloid from the Mexican wild potatoSolanum demissum Lindl. The synthesis involves the following steps: 5-solanidane-3-one, 2,4-dibromo-5-solanidane-3-one, solanid-4-ene-3-one, 3-acetoxy-solanida-3,5-diene, and solanidine (II).

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Solanum-Alkaloide. XVII. Mitteilung. — XVI. Mitteilung:K. Schreiber undG. Adam, Exper.17, 490 (1961).     

Hydrolysis of amino acid β-naphthylamides by aminopeptidases in the parotid gland

Zusammenfassung Die Aktivität der Aminopeptidasen in Ohrspeicheldrüsen wurde gemessen. Glycyl-Prolin-naphthylamid, Alanin-naphthylamid, Leucin-naphthylamid, Methionin-naphthylamid, und Arginin-naphthylamid wurden von der Mikrosomenfraktion und der löslichen Fraktion schnell gespalten. Das Glycyl-Prolin-naphthylamid spaltende Enzym war in Ohrspeicheldrüsen in relativ grösserer Menge vorhanden. Die Aufspaltung von Glycyl-Prolin-naphthylamid in Glycyl-Prolin und-Naphthylamin wurde papierchromatographisch nachgewiesen.     

Caractérisation de laβ-galactosidase d'Helix pomatia par immunoélectrophorèse

Summary Digestive juice ofHelix pomatia was studied by immunoelectrophoresis: after incubation with a chromogenic substrate, 5-bromo-4-chloroindol-3-yl--D-galactopyranoside, two-galactosidases were revealed.     

Solid-phase synthesis of lysine vasopressin analogs: [1-β-mercaptopropionic acid, 8-lysine]-vasopression and [1-β-mercaptopropionic acid, 8-(ε-N-p-toluenesulfonyl)-lysine]-vasopressin

Zusammenfassung Mit Hilfe der Festkörpermethode nachMerrifield wird die Synthese von [1--Mercaptopropionsäure, 8-lysin]-Vasopressin und [1--Mercaptopropionsäure, 8-(-N--toluälsulfonyl)-lysin]-Vasopressin, beschrieben. In diesen Analogen sind die potentiellen Kationenzentren des antidiuretischen Hormons Lysin-Vasopressin schrittweise entfernt worden.

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Supported by USPHS Grants Nos. AM-13567 and AM-10080.

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Abbreviations follow the rules of the IUPAC-IUB Commission on Biochemical Nomenclature in Biochemistry6, 362 (1967).     

The characteristic specificity of plasmocytoma lipids concerning their resistance to formdl-fractions with colloidal dextran

Zusammenfassung Papierelektrophoretische Lipiduntersuchungen von- und-Plasmacytom — Paraproteinseren nach Kolloidaldextranbelastung erfassen eine neue, in der Diagnostik des Plasmocytoms verwertbare Eigenschaft: die Paraproteinlipidkomponente (PL) vermag, entgegen den-Lipoproteinen, mit Dextran keine Assoziationsfraktion zu bilden.

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My thanks are due toJosipa Franjkovi for her technical assistance.     

Fucosidases du suc digestif d'Helix pomatia

Summary The-d-fucosidase and -l-fucosidase activities of digestive juice ofHelix pomatia have been studied.-d-fucosidase can be separated from-d-galactosidase by heat inactivation.     

7α-hydroxylation of dehydroepiandrosterone in human testis and epididymis in vitro

Zusammenfassung Zerhackte menschliche Hoden und Epididymis wurden mit Dehydroepiandrosteron ohne Kofaktoren bebrütet und es wurden unter anderem 7-und 7-Hydroxydehydroepiandrosteron und 5-Androsten-3, 7, 17-triol charakterisiert. Die Ausbeute an 7-hydroxylierten Metaboliten war fast gleich in Hoden und Epididymis.

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The authors wish to thank Mr.J. Novák for his excellent technical assistance. We are indebted to Dr.J. E. Jirásek for generous performance of histological control of tissue and to Dr.S. Röhling for his kind pernission of radioactivity measurements.     

Neue Synthesen des Chloramphenicols und deren stereochemischen Beziehungen

Summary Two new syntheses of Chloramphenicol are described starting from the diastereoisomers of -phenylserinmethyl ether and cinnamyl alcohol methyl ether respectively. The configurational correlation of the diastereoisomers of -phenylserin-methyl ether with -phenylserin and chloramphenicol is discussed. A new method for transforming erythro--phenylserinol into threo--phenylserinol is described. New examples of the Neighboring group effect were studied. The sterical course of the addition of methylhypobromite to the double bond is discussed.     

The synthesis of stereoselectively labelled porphobilinogen and its incorporation into protoporphyrin-IX

Summary 11-(R)-²H porphobilinogen, stereospecifically labelled with deuterium in the aminomethylene group has been incorporated into protoporphyrin-IX by haemolysates of chicken erythrocytes. High field NMR spectroscopy confirms that the overall biochemical process is stereospecific, deuterium being retained at the -, -and -meso positions and lost from the -meso position.27 August 1986     

1β-Hydroxylation ofd-norgestrel and norethisterone byBotryodiploadi malorum

Zusammenfassung Die mikrobiologische 1-Hydroxylierung vond-Norgestrel und Norethisteron durch den MikroorganismusBotryodiplodia malorum wird beschrieben. Ausserdem wurde 11-Hydroxynorethisteron isoliert und charakterisiert.

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Acknowledgement. The authors want to express their appreciation to Dr.H. Smith for advice and encouragement through the course of this work. We wish to thank Dr.T. Chang, Dr.C. Hetzel and Mr.C. Kuhlman for obtaining and interpreting the mass spectra and Mr.B. Hormann for NMR decoupling experiments and analytical services.     

Über die Ausscheidung von 3β-Hydroxy-17-Ketosteroiden im Harn von Meerschweinchen

Summary 11-hydroxy-epiandrosterone was isolated and identified from urine of normal untreated female guinea pigs. After cold and hot acid hydrolysis of the urine, we found another 3-hydroxy-17-oxosteroid. Its character was investigated by several methods and we suppose this steroid is9(11)-epiandrosterone, an artificial product of 11-hydroxy-epiandrosterone.     

Konstitution des Cinobufagins

Summary The structure of Cinobufagin is shown to be 3-Hydroxy-14, 15-epoxy-16-acetoxy-5-bufa-20, 22-dienolide.

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Die ausführliche Publikation erscheint demnächst in den Helv. chim. Acta.     

Comparative analysis of human milk and human blood plasma by means of diffusion-in-gel methods

Zusammenfassung Mit Hilfe von Immunoelektrophorese und Doppeldiffusiontechnik wurden in Humanmilch an Blutplasmaproteinen serologisch identifiziert: Praealbumin, Albumin, Acid Seromucoid, ₁-Glykoprotein (3·5 S), Coeruloplasmin, Haptoglobin, ₂- oder-Lipoprotein, Transferrin, Fibrinogen, _2A-Globulin, _2M-Globulin und-Globulin.     

The formation of androgens in human foetal liver in vitro

Zusammenfassung Nach Inkubation des homogenisierten Lebergewebes menschlicher, 7–20 Wochen alter, Foeten mit 3-Hydroxy-5-androsten-17-on wird die Bildung von Testosteron, 4-Androsten-3, 17-dion und 5-Androsten-3, 17-diol nachgewiesen.     

Wirkung von 6β-Methoxy-9β,10α-pregna-4,6-dien-3,20-dion

Summary 6-Methoxy-9,10 -pregna-4,6-diene-3,20-dione inhibites the ⁴-3-oxosteroid-5-reduction in microsomes and the ⁴-3-oxosteroid-5-reduction in the soluble fraction of male rat liver. The 3- and 3-hydroxysteroid dehydrogenase are not inhibited by this substance.

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Diese Arbeit wurde von der Firma Hoffmann-La Roche, Basel, unterstützt.     

Uptake of D-glucose anomers by rat retina

Summary Uptake ofd-glucose anomers by isolated rat retina was studied. After 3 min incubation at 37°C in the presence of or anomer (750 g/ml), a significantly greater uptake (1.32 mg/g wet tissue) of -anomer was observed compared with that of -d-glucose (1.11 mg/g wet tissue). This result and other data suggest that the carrier ford-glucose transport in the retina prefers the -anomer stereospecifically.Acknowledgment. The authors are grateful to Mr S. Suzuki for his technical assistance.     

The effects of γ-aminobutyric acid and picrotoxin on the junctional potential and the contraction of crayfish muscle

Résumé L'acide-amino-butyrique et la-alanine reproduisent l'action du transmetteur inhibiteur du système neuromusculaire de l'écrevisse. Ces deux acids aminés diminuent la contraction musculaire. L'acide-amino-butyrique réduit la différence de potentiel et augmente sa décomposition. L'action de ces acides aminés est bloquée par la picrotoxine comme l'est celle du transmetteur inhibiteur.

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The study was supported by Grants B-1089 and B-31 from the National Institute of Neurological Diseases and Blindness, United States Public Health Service. Some of this work was done at the Department of Zoology, Cornell University. We are grateful to Prof.S. C. Wang, Columbia University, for generous assistance.