Über Peptidsynthesen. C-terminale Teilsequenzen des Eledoisins und eledoisinanaloger Verbindungen

Summary A series of synthetic Eledoisin and Eledoisin-related subunits are described. The biological activities of the peptides are discussed.

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Über Peptidsynthesen XXIII. 2. Mitt. über Eledoisin und Eledoisinanaloga. 1. Mitt. siche⁹.

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B. Camerino, G. de Caro, R. A. Boissonnas, Ed. Sandrin undE. Stürmer, Exper.19, 339 (1963).     

Voacanga-Alkaloide IV. Struktur von Voacryptin und Voacristin

Summary Voacryptine is demonstrated to be 20-oxovoacangine. On reduction, it furnishes voacristine (20-hydroxyvoacangine) and 20-epi-voacristine.

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3. Mitt.U. Renner undD. A. Prins, Exper.15, 456 (1959).     

Über die Herkunft der Isovaleriansäure im Magnamycin

Summary L-Leucine is the precursor of the isovaleric acid in magnamycin, as could be demonstrated withL-Leucine-[U-¹⁴].

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IX. Mitt. Zur Biogenese der Makrolide. VIII. Mitt.W. Hofheinz, H. Grisebach undH. Friebolin, Tetrahedron, im Druck.     

Über eine neue Synthese von 18-Hydroxy- und 18-Oxo-progesteron

Summary 18-Hydroxyprogesterone (VII) and the corresponding 18-aldehyde (IX), hitherto only accessible with difficulty from natural 18-substituted steroids, have been synthesized starting from progesterone.

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Über Steroide, 188. Mitt.

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187. Mitt. s.Ch. Meystre, K. Heusler, J. Kalvoda, P. Wieland, G. Anner undA. Wettstein, Helv. chim. Acta45, 1317 (1962).     

über Peptidsynthesen,XLVI. Synthese kininliefernder Kininogensequenzen

Summary H-Met-Lys-bradykinin-Ser-Val-Gln-OH and H-Met-Lys-bradykinin- Ser-Val-Gin-Val-OH, sequences of bovine serum kininogen have been synthetized by different approaches. The natural and synthetic peptides were tested for their kinin liberating potency.

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XLV. Mitt.: E.Klieger, Justus Liebigs Ann. Chem.,724, 204 (1969).     

Zur Pathogenese des Urämiesyndroms1. Über den Einfluss von Tyramin auf die Acetoinsynthese aus Brenztraubensäure in Rattenleberhomogenat2

Summary Tyramine enhanced the production of acetoin from pyruvate in rat liver homogenates. A stimulation of acetoin synthesis was only observed, when tyramine was oxidized during the incubation. Tyrosol (p-hydroxyphenylethanol) stimulated acetoin synthesis whereasp-hydroxyphenylacetic acid and ammonia were ineffective.

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Mit Unterstützung des »Schweizerischen Nationalfonds» und der Firma F. Hoffmann-La Roche & Co. AG, Basel.

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8. Mitteilung. 1. Mitt.:H. Thölen, F. Bigler undH. Staub, Path. Microbiol. (Basel)24, 262 (1961). — 2. Mitt.:F. Bigler, H. Thölen undH. Staub, Helv. physiol. Acta19, C 11 (1961). — 3. Mitt.:H. Thölen, F. Bigler undH. Staub, Exper.17, 359 (1961). — 4. Mitt.:F. Bigler, H. Thölen undH. Staub, Schweiz. med. Wschr.91, 1259 (1961). — 5. Mitt.:H. Thölen, F. Bigler, A. Heusler, W. Stauffacher undH. Staub, Exper.18, 454 (1962). — 6. Mitt.:F. Bigler, H. Thölen undH. Staub, Schweiz. med. Wschr.92, 746 (1962). — 7. Mitt.:F. Bigler, H. Thölen undH. Staub, in Vorbereitung.     

Zur Pathogenese des Urämiesyndroms. Brenztraubensäure,Acetoin und 2,3-Butylenglykol in Blut von Patienten mit Nieren- und Leberkrankheiten

Summary Acetoin and 2, 3-butylene glycol in blood of renal and hepatic patients are raised, when consciousness is disturbed. There is no correlation between blood levels of acetoin and 2, 3-butylene glycol and the degree of impairment of consciousness. Simultaneous determinations of acetoin and 2, 3-butylene glycol in blood and cerebrospinal fluid show that alterations of the cerebral pyruvic acid metabolism are difficult to detect in circulating blood.

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Mit Unterstützung des «Schweizerischen Nationalfonds» und der Firma F. Hoffmann-La Roche & Co., AG, Basel.

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5. Mitteilung. — 1. Mitt.:H. Thölen, F. Bigler undH. Staub, Path. Microbiol.24, 262 (1961). — 2. Mitt.:F. Bigler, H. Thölen undH. Staub, Helv. physiol. Acta19, C11 (1961). — 3. Mitt.:H. Thölen, F. Bigler undH. Staub, Exper.17, 359 (1961). — 4. Mitt.:F. Bigler, H. Thölen undH. Staub, Schweiz. med. Wschr.91, 1259 (1961).     

Über den Einfluss der Kettenlänge auf die biologische Aktivität eledoisinanaloger Verbindungen

Summary The syntheses of Eledoisin analogues by shortening the peptide chain at the N-terminal moiety of the molecule are described. The influence of the chain length on the hypotensive activity is discussed.

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Über Peptidsynthesen XXXII. 5. Mitt. über Eledoisin und Eledoisin-Analoga. 4. Mitt. sieheE. Schröder, K. Lübke undR. Hempel, Exper.21, 70 (1965).

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Auszugsweise vorgetragen auf dem 7. Europäischen Peptidsymposium in Budapest (Sept. 1964).     

Synthese und biologische Aktivität bradykininwirksamer Undeca-, Dodeca- und Tridecapeptide

Summary Several undeca-, dodeca- and tridecapeptides, analogues of the naturally occurring methionyllysyl-bradykinin, have been synthesized. The biological activities of the new compounds on the isolated rat uterus, guinea-pig ileum and rabbit blood pressure are presented.

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über Peptidsynthesen XXXIV. 7. Mitt. über Bradykinin- und Kallidin-Analoga. XXV. Mitt. über Peptidsynthesen, 6. Mitt. über Bradykinin- und Kallidin-Analoga:E. Schr?der, H.-S. Petras undE. Klieger, Liebigs Ann.679, 221 (1964).     

Nachweis von Scilliglaucosidin in den Zwiebeln vonBowiea volubilis Harvey

Summary Hellebrigenin was converted to Scilliglaucosidin-19-ol and 3-Epi-Scilliglaucosidin-19-ol. This proves the correctness of the assumption ofStoll et al. ³ that the aldehydic group of Scilliglaucosidin is in position C-10.Comparison of a reduction product of Nabogenin, a substance isolated earlier from the bulbs ofBowiea volubilis Harvey, with Scilliglaucosidin-19-ol and 3-Epi-Scilliglaucosidin-19-ol showed its identity with the first named compound. This proves that the so called Nabogenin was a mixture consisting mainly of Scilliglaucosidin.

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8. Mitteilung über die Glykoside vonBowiea vocubilis Harvey und 162. Mitteilung über Glykoside und Aglykone.

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7. Mitt.:A. Katz, Helv. chim. Acta38, 1565 (1955).

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161. Mitt.:H. Kündig-Hegedüs undO. Schindler, Helv. chim. Acta39, 904 (1956).     

Phtalocyanine in wässriger Lösung. Zum Mechanismus der Metallkomplexbildung

Summary The mechanism of incorporation of different mental ions into phthalocyaninetetrasulfonic acid in aqueous solution has been investigated. It was found that the rate of the reacion with Cu²⁺ depends on the dissociation rate of the N-H-bond of this porphyrin-like chelating agent, whereas the reaction rate with other metal ions, like Zn²⁺, does not.

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II. Mitt. Siehe I. Mitt.:K. Bernauer undS. Fallab, Helv.44, 1287 (1961).

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Herrn Prof. Dr.H. Erlenmeyer sind wir für sein reges Interesse an dieser Arbeit zu bestem Dank verpflichtet.     

Enzymatische Hydrierungen im Ring A von Steroiden mittels Streptomyzeten

Summary A strain ofStreptomyces griseus has been found to convert ⁴-3-keto steroids into the corresponding saturated 3-keto-5-compounds and, on prolonged incubation, into the 3-hydroxy-5-derivatives.

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10. Mitt. über mikrobiologische Reaktionen; 9. Mitt. sieheJ. Urech, E. Vischer undA. Wettstein, Helv. chim. Acta43, 1077 (1960).

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170. Mitt. über Steroide; 169. Mitt. sieheR. Neher undA. Wettstein, Helv. chim. Acta43, 1171 (1960).

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Auszugsweise vorgetragen am VII. Internationalen Kongress für Mikrobiologie, Stockholm 1958.     

Bazzanenol,a new sesquiterpene alcohol having a skeleton of Bicyclo[5.3.1] undecane system from hepaticae,Bazzania pompeana (Lac.) Mitt

Zusammenfassung Isolierung und Strukturaufklärung eines neuen Sesquiterpenalkohols ausBazzania pompeana (Lac.) Mitt.

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Studies on chemical constituents from Hepaticae, Part III: S.Hayashi, A.Matsuo and T.Matsuura, Tetrahedron Letters,1969, 1599 and ref.² are regarded as Part I and II.     

Synthetische Versuche in der Doisynolsäurereihe

Summary The amorphous carboxylic acid of the doisynolic acid type, prepared byHunter andHogg according to a new method developed by us, consists presumably of a mixture of products representing different hydrogenation stages.

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54. Mitt. «Über Steroide» sowie XI. Arbeit «Über östrogene Karbonsäuren». Vgl. Exper.2, 408 (1946) und Helv. chim. acta29, 1231 (1946).     

d-Aminosäurehaltige Analoga des Eledoisins

Summary The synthesis of several C-terminal eledoisin heptapeptide analogues, containing 1–5d-amino acids, is described and the biological activities are discussed.

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Über Peptidsynthesen XXXI. 4. Mitt. über Eledoisin und Eledoisin-Analoga. 3. Mitt. über Eledoisin und Eledoisin-Analoga:K. Lübke undE. Schröder, Liebigs Ann., im Druck.

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Auszugsweise vorgetragen auf dem VII. Europäischen Peptidsymposium, September 1964 in Budapest.     

Über ein gebundenes Gibberellin ausPhaseolus coccineus L.

Summary In addition to gibberellins A₁, A₅, A₆ and A₈ previously isolated fromPhaseolus coccineus L., the occurrence of gibberellin A₃ and of 5 new gibberellin-like substances «Phaseolus -» was demonstrated. «Phaseolus» was proved to be a gibberellin bound to carbohydrates and ninhydrin-positive compounds.

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Gibberelline, II. Mitteilung. — I. Mitt. sieheG. Sembdner, R. Gross undK. Schreiber, Exper.18, 584 (1962).     

Dien-Synthesen im Aufbau von Östrogenen

Summary The addition of citraconic anhydride to 1-vinyl-6-methoxy-3,4-dihydro-naphthalene according toDiels-Alder's method yielded two isomeric hydro-phenanthrene-dicarboxylic acids. One of these two acids has been converted into 2-methyl-7-methoxy-1,2,3,4,9,10-hexahydro-1,2-dicarboxylic-acid.

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Mitteilung « Über Steroide » (65. Mitt. siehe Helv. chim. Acta30, 1037 [1947]), sowie XX. Arbeit « Über östrogene Carbonsäuren » (XIX. siehe Exper.3, 279 [1947]).     

Synthetic peptides related to caerulein1. Note 1

Riassunto Vengono descritte le proprietà di una serie di peptidi sintetici affini alla ceruleina e si discutono brevemente i rapporti fra attività e struttura.

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A. Anastasi, V. Erspamer andR. Endean, Experientia23, 699 (1967).

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This work was in part supported by grants from the Consiglio Nazionale delle Ricerche, Roma.