Collect. Czech. Chem. Commun. 1955, 20, 1183-1189
https://doi.org/10.1135/cccc19551183

Synthetic studies in the oxytocin field. I. A synthesis of S-benzyl-L-cysteinyl-L-prolyl-L-leucylglycine amide

M. Zaoral and J. Rudinger

Individual author index pages


Other CCCC articles of these authors

  • M. Zaoral and I. Bláha
    [1-β-Mercaptopropionic acid, 4-asparagine,8-D-arginine]vasopressin, an analogue with a high and very pure antidiuretic activity
    1977, Vol. 42, Issue 12, pp. 3654–3657 [Abstract]
  • M. Zaoral and V. Krchňák
    Cyclooxytocin, an oxytocin analogue with an enhanced stability of the secondary structure
    1977, Vol. 42, Issue 12, pp. 3500–3509 [Abstract]
  • R. Straka and M. Zaoral
    Synthesis of isoglutamine, isoasparagine, and derivatives
    1977, Vol. 42, Issue 2, pp. 560–563 [Abstract]
  • F. Brtník and M. Zaoral
    Synthesis of derivatives and peptides of α-amino-β-guanidinopropionic acid and α-amino-γ-guanidinobutyric acid
    1976, Vol. 41, Issue 10, pp. 2969–2977 [Abstract]
  • M. Zaoral, F. Brtník, T. Barth and A. Machová
    [1-β-Mercaptopropionic acid, 8-α,γ-diaminobutyric acid]vasopressin and [1-β-mercaptopropionic acid, 8-D-ornithine]vasopressin. Synthesis and biological effects
    1976, Vol. 41, Issue 7, pp. 2088–2095 [Abstract]
  • I. Frič, M. Buděšínský, F. Brtník and M. Zaoral
    The conformation of C-terminal tripeptides of neurohypophysial hormones. Proton magnetic resonance and circular dichroic studies
    1976, Vol. 41, Issue 6, pp. 1704–1713 [Abstract]
  • M. Zaoral and F. Brtník
    Preparation of [1-β-mercaptopropionic acid, 8-homoarginine]-, and [1-β-mercaptopropionic acid, 8-D-homoarginine]-vasopressin
    1975, Vol. 40, Issue 3, pp. 905–912 [Abstract]
  • F. Brtník, A. Trka and M. Zaoral
    Thermal stability of vasopressin-(7-9)-, and oxytocin-(7-9)-tripeptide amides
    1975, Vol. 40, Issue 1, pp. 179–186 [Abstract]
  • M. Zaoral, I. Laine and F. Brtník
    [4-Leucine, 8-D-arginine]- and [1-β-mercaptopropionic acid, 4-leucine, 8-D-arginine]-vasotocin. Two vasotocin analogs with specific antidiuretic effect
    1974, Vol. 39, Issue 10, pp. 2975–2985 [Abstract]
  • M. Zaoral and M. Flegel
    [1-β-Mercaptopropionic acid, 8-D-norarginine]-vasopressin. A further analog with high and specific antidiuretic effect
    1972, Vol. 37, Issue 10, pp. 3350–3351 [Abstract]
  • M. Zaoral and M. Flegel
    Amino acids and peptides. CVIII. Desaminovasopressin-(1-6)- and desaminooxytocin-(1-6)-hexapeptide amide
    1972, Vol. 37, Issue 8, pp. 2639–2643 [Abstract]
  • M. Zaoral and M. Flegel
    Amino acids and peptides. CVI. Cyclic part of vasopressin and oxytocin molecule; Synthesis and biological properties
    1972, Vol. 37, Issue 5, pp. 1539–1545 [Abstract]
  • M. Zaoral
    Isoleucyl-alanyl-p-aminobenzoic acid ethyl ester. A compound showing the activity of juvenile hormone and the properties of a local anesthetic
    1971, Vol. 36, Issue 5, pp. 2080–2082 [Abstract]
  • M. Zaoral, J. Kolc and F. Šorm
    Amino acids and peptides. XCVII. [8-α,β-Diaminopropionic acid]-, [8-D-α,β-diaminopropionic acid]-, and [8-D-ornithine]-vasopressin
    1970, Vol. 35, Issue 6, pp. 1716–1726 [Abstract]
  • M. Hudlický, V. Jelínek, K. Eisler and J. Rudinger
    Organic compounds of fluorine. XIV. The synthesis and configuration of ω-fluoroalloisoleucine
    1970, Vol. 35, Issue 2, pp. 498–503 [Abstract]
  • K. Bláha, I. Frič and J. Rudinger
    Amino acids and peptides. XCIV. Optical rotatory properties of diastereomeric cyclohexapeptides containing glycine, leucine, and phenylalanine
    1969, Vol. 34, Issue 11, pp. 3497–3509 [Abstract]
  • E. Kasafírek, K. Eisler and J. Rudinger
    Amino acids and peptides. XCII. Synthesis of [1-β-mercaptopropionic acid, 2-O-methyltyrosine]oxytocin (desamino-methyloxytocin)
    1969, Vol. 34, Issue 9, pp. 2848–2852 [Abstract]
  • K. Poduška, J. Rudinger, J. Gloede and H. Gross
    Aminosäuren und Peptide. XC. Synthese des β-Pyrrolo-L-alanins, der L-2-Amino-4-pyrrolobuttersäure und der L-2-Amino-5-pyrrolovaleriansäure
    1969, Vol. 34, Issue 3, pp. 1002–1006 [Abstract]
  • J. Krupička and M. Zaoral
    Amino acids and peptides. LXXXVIII. Polarography of lysine-vasopressin and of some vasopressin analogs
    1969, Vol. 34, Issue 2, pp. 678–681 [Abstract]
  • H.-D. Jakubke, J. Fischer, K. Jošt and J. Rudinger
    Amino acids and peptides. LXXXVI. Synthesis of L-selenomethionine, L-selenoethionine and their tert-butyloxycarbonyl derivatives
    1968, Vol. 33, Issue 11, pp. 3910–3912 [Abstract]
  • H. Nesvadba, K. Jošt, J. Rudinger and F. Šorm
    Amino acids and peptides. LXXXV. Synthesis of [Ser1,Ser6]-oxytocin
    1968, Vol. 33, Issue 11, pp. 3790–3795 [Abstract]
  • A. Chimiak, K. Eisler, K. Jošt and J. Rudinger
    Amino acids and peptides. LXXX. Unambiguous syntheses of N-carbamyl-oxytocin and N-carbamyl-2-O-methyltyrosine-oxytocin
    1968, Vol. 33, Issue 9, pp. 2918–2926 [Abstract]
  • J. Gloede, K. Poduška, H. Gross and J. Rudinger
    Amino acids and peptides. LXXIX. α-Pyrrolo analogues of α-amino acids
    1968, Vol. 33, Issue 4, pp. 1307–1314 [Abstract]
  • L. Mladenova-Orlinova, K. Bláha and J. Rudinger
    Amino acids and peptides. LXXVII. Further diastereomeric cyclohexapeptides containing glycine, phenylalanine and leucine; Configurational conditions for the presence of cis peptide bonds
    1967, Vol. 32, Issue 11, pp. 4070–4081 [Abstract]
  • J. Kolc, M. Zaoral and F. Šorm
    Amino acids and peptides. LXXV. Synthesis of Gly7-Lys8-vasopressin and D-Pro7-Lys8-vasopressin
    1967, Vol. 32, Issue 7, pp. 2667–2671 [Abstract]
  • K. Jošt and J. Rudinger
    Amino acids and peptides. LXXIV. Derivatives of L-cystathionine suitable for peptide synthesis
    1967, Vol. 32, Issue 7, pp. 2485–2490 [Abstract]
  • K. Bláha and J. Rudinger
    Amino acids and peptides. LXXIII. Stereoisomeric tripeptides and hexapeptides containing glycine, phenylalanine, and leucine
    1967, Vol. 32, Issue 6, pp. 2365–2370 [Abstract]
  • P. J. Thomas, M. Havránek and J. Rudinger
    Amino acids and peptides. LXXII. Synthesis of 2-phenylalanine-[U-14C]-8-lysine-vasopressin
    1967, Vol. 32, Issue 5, pp. 1767–1775 [Abstract]
  • M. Zaoral, J Kolc and F. Šorm
    Amino acids and peptides. LXXI. Synthesis of 1-deamino-8-D-γ-aminobutyrine-vasopressin, 1-deamino-8-D-lysine-vasopressin, and 1-deamino-8-D-arginine-vasopressin
    1967, Vol. 32, Issue 3, pp. 1250–1257 [Abstract]
  • M. Zaoral, J. Kolc and F. Šorm
    Amino acids and peptides. LXX. Synthesis of D-Arg8- and D-Lys8-vasopressin
    1967, Vol. 32, Issue 3, pp. 1242–1249 [Abstract]
  • K. Jošt and J. Rudinger
    Amino acids and peptides. LXIX. Synthesis of two biologically active analogues of deamino-oxytocin not containing a disulphide bond
    1967, Vol. 32, Issue 3, pp. 1229–1241 [Abstract]
  • M. Zaoral, J. Kolc, F. Korenczki, V. P. Černěckij and F. Šorm
    Amino acids and peptides. LXVIII. Preparation of three lysine-vasopressin analogs modified at position 9; D-Ala9-lysine-vasopressin, Ala9-lysine-vasopressin, and 9-ethylenediamine-lysine-vasopressin
    1967, Vol. 32, Issue 2, pp. 843–853 [Abstract]
  • E. Kasafírek, V. Rábek, J. Rudinger and F. Šorm
    Amino acids and peptides. LXVI. Synthesis of ten extended-chain analogues of lysine vasopressin
    1966, Vol. 31, Issue 12, pp. 4581–4591 [Abstract]
  • K. Eisler, J. Rudinger and F. Šorm
    Amino acids and peptides. LXV. Analogues of oxytocin with isoleucine replaced by L-diethylalanine, L-cyclopentylglycine, and L- and D-cyclohexylglycine
    1966, Vol. 31, Issue 12, pp. 4563–4580 [Abstract]
  • K. Poduška and J. Rudinger
    Amino acids and peptides. LXII. Synthesis of a protected cyclodecapeptide containing α,γ-diaminobutyric acid
    1966, Vol. 31, Issue 7, pp. 2938–2954 [Abstract]
  • M. Zaoral, J. Kolc and F. Šorm
    Synthesis of D-Arg8- and D-Lys8-vasopressin
    1966, Vol. 31, Issue 1, pp. 382–383 [Abstract]
  • M. Zaoral and F. Šorm
    Amino acids and peptides. LX. Synthesis of D-Dab8-vasopressin
    1966, Vol. 31, Issue 1, pp. 310–314 [Abstract]
  • M. Zaoral and F. Šorm
    Amino acids and peptides. LIX. Synthesis and some biological properties of L-DAB8-vasopressin
    1966, Vol. 31, Issue 1, pp. 90–97 [Abstract]
  • K. Bláha and J. Rudinger
    Amino acids and peptides. LVIII. Cyclisation of peptides with 2-ethyl-5-phenylisoxazolium-3'-sulphonate
    1965, Vol. 30, Issue 10, pp. 3325–3332 [Abstract]
  • H. Farkašová and J. Rudinger
    Amino acids and peptides. LVII. A synthesis of L-α-aminopimelic and L-α-aminosuberic acid
    1965, Vol. 30, Issue 9, pp. 3117–3122 [Abstract]
  • P. Hermann and M. Zaoral
    Aminosäuren und Peptide LVI. Synthese von Thialysin8-vasopressin
    1965, Vol. 30, Issue 8, pp. 2817–2826 [Abstract]
  • M. Zaoral and F. Šorm
    Amino acids and peptides. LV. Synthesis of Gly-Cys1-lysine-vasopressin and Gly-Cys1-Tyr(Me)2-lysine-vasopressin
    1965, Vol. 30, Issue 8, pp. 2812–2816 [Abstract]
  • E. Kasafírek, K. Jošt, J. Rudinger and F. Šorm
    Amino acids and peptides. LIV. Synthesis of further extended-chain analogues of oxytocin
    1965, Vol. 30, Issue 8, pp. 2600–2608 [Abstract]
  • A. Chimiak and J. Rudinger
    Amino acids and peptides. LIII. Synthesis and some biological properties of 3-O-methyl-threonine-oxytocin
    1965, Vol. 30, Issue 8, pp. 2592–2599 [Abstract]
  • K. Poduška, G. S. Katrukha, A. B. Silaev and J. Rudinger
    Amino acids and peptides. LII. Intramolecular aminolysis of amide bonds in derivatives of α,γ-diaminobutyric acid, α,β-diaminopropionic acid, and ornithine
    1965, Vol. 30, Issue 7, pp. 2410–2433 [Abstract]
  • M. Zaoral, E. Kasafírek, J. Rudinger and F. Šorm
    Amino acids and peptides. LI. Synthesis of 2-O-methyltyrosine- and 2-O-ethyltyrosine-lysine-vasopressin
    1965, Vol. 30, Issue 6, pp. 1869–1873 [Abstract]
  • M. Zaoral
    Amino acids and peptides. L. Synthesis of Asp(NH2)4-lysine-vasopressin; A new synthesis of lysine-vasopressin
    1965, Vol. 30, Issue 6, pp. 1853–1868 [Abstract]
  • M. Zaoral and F. Šorm
    The preparation and certain biological properties of L-Dab8-vasopressin and D-Dab8-vasopressin
    1965, Vol. 30, Issue 2, pp. 611–612 [Abstract]
  • K. Bláha and J. Rudinger
    Amino acids and peptides. XLVIII. Rates of fission of some cycloalkyloxycarbonylglycines with hydrogen bromide in acetic acid
    1965, Vol. 30, Issue 2, pp. 599–604 [Abstract]
  • K. Bláha and J. Rudinger
    Amino acids and peptides. XLVII. Rates of fission of some substituted benzyloxycarbonylglycines and two heterocyclic analogues with hydrogen bromide in acetic acid
    1965, Vol. 30, Issue 2, pp. 585–598 [Abstract]
  • A. L. Zhuze, K. Jošt, E. Kasafírek and J. Rudinger
    Amino acids and peptides. XLV. Analogues of oxytocin with O-ethyltyrosine, p-methylphenylalanine, and p-ethylphenylalanine replacing tyrosine
    1964, Vol. 29, Issue 11, pp. 2648–2662 [Abstract]
  • Yang Chen-Su, K. Bláha and J. Rudinger
    Amino acids and peptides. XLIV. Synthesis of three diastereomeric cyclohexapeptides containing glycine, phenylalanine and leucine
    1964, Vol. 29, Issue 11, pp. 2633–2647 [Abstract]
  • K. Jošt, V. G. Debabov, H. Nesvadba and J. Rudinger
    Amino acids and peptides. XLII. A synthesis of dethiooxytocin and other acyclic peptides related to oxytocin
    1964, Vol. 29, Issue 2, pp. 419–432 [Abstract]
  • V. Gut and J. Rudinger
    Amino acids and peptides. XLI. New methods for the synthesis of derivatives and peptides of α-aminoadipic acid
    1963, Vol. 28, Issue 11, pp. 2953–2968 [Abstract]
  • J. Rudinger and H. Farkašová
    Amino acids and peptides. XL. Synthesis of L-α-aminoadipic acid and L-β-aminoadipic acid from L-glutamic acid
    1963, Vol. 28, Issue 11, pp. 2941–2952 [Abstract]
  • K. Jošt, J. Rudinger and F. Šorm
    Amino acids and peptides. XXXIX. Analogues of oxytocin exerting protracted biological effects
    1963, Vol. 28, Issue 8, pp. 2021–2030 [Abstract]
  • K. Jošt, J. Rudinger and F. Šorm
    Amino acids and peptides. XXXVIII. Structural analogues of oxytocin modified in position 2 of the peptide chain: Preparation and some chemical and biological properties
    1963, Vol. 28, Issue 7, pp. 1706–1714 [Abstract]
  • H. Nesvadba, J. Honzl and J. Rudinger
    Amino acids and peptides. XXXVII. Some structural analogues of oxytocin modified in position 3 of the peptide chain: Synthesis and some chemical and biological properties
    1963, Vol. 28, Issue 7, pp. 1691–1705 [Abstract]
  • M. Zaoral, V. Pliška, K. Řežábek and F. Šorm
    Synthesis of two lysine-vasopressin analogues with protracted hormonal activity
    1963, Vol. 28, Issue 3, pp. 747–749 [Abstract]
  • M. Zaoral, V. Pliška, K. Řežábek and F. Šorm
    Synthesis of a highly effective analogue of lysine-vasopressin
    1963, Vol. 28, Issue 3, pp. 746–747 [Abstract]
  • M. Zaoral
    Amino-acids and peptides. XXXVI. Pivaloyl chloride as a reagent in the mixed anhydride synthesis of peptides
    1962, Vol. 27, Issue 5, pp. 1273–1277 [Abstract]
  • Z. Beránková, I. Rychlík, K. Jošt, J. Rudinger and F. Šorm
    Inhibition of the uterus-contracting effect of oxytocin by O-methyloxytocin
    1961, Vol. 26, Issue 10, pp. 2673–2675 [Abstract]
  • K. Jošt, J. Rudinger and F. Šorm
    Amino-acids and peptides. XXXV. Analogues of oxytocin modified in positions 1 and 2 of the peptide chain: Protected intermediates
    1961, Vol. 26, Issue 10, pp. 2496–2510 [Abstract]
  • K. Jošt and J. Rudinger
    Amino-acids and peptides. XXXIV. Some peptides of S-benzylcysteine
    1961, Vol. 26, Issue 9, pp. 2345–2354 [Abstract]
  • J. Honzl and J. Rudinger
    Amino-acids and peptides. XXXIII. Nitrosyl chloride and butyl nitrite as reagents in peptide synthesis by the azide method; Suppression of amide formation
    1961, Vol. 26, Issue 9, pp. 2333–2344 [Abstract]
  • M. Zaoral and J. Rudinger
    Amino-acids and peptides. XXXI. Products formed from tosylglycine under the conditions of a mixed carbonic anhydride synthesis
    1961, Vol. 26, Issue 9, pp. 2316–2332 [Abstract]
  • J. Rudinger, J. Krupička, M. Zaoral and V. Černík
    Amino-acids and peptides. XXX. Alkaline hydrolysis of the phthalimido group in phthalylamino-acids and their derivatives; A polarographic study
    1960, Vol. 25, Issue 12, pp. 3338–3343 [Abstract]
  • J. Rudinger, K. Poduška and M. Zaoral
    Amino-acids and peptides. XXIX. Synthesis of the lower homologues of L-arginine and L-citrulline
    1960, Vol. 25, Issue 8, pp. 2022–2028 [Abstract]
  • J. Sicher, M. Rajšner, J. Rudinger, M. Eckstein and F. Šorm
    Amino-acids and peptides. XXVIII. Synthesis of threo- and erythro-DL-α,γ-diamino-β-hydroxybutyric acid (γ-aminothreonine and γ-aminoallothreonine)
    1959, Vol. 24, Issue 11, pp. 3719–3729 [Abstract]
  • K. Poduška and J. Rudinger
    Amino-acids and peptides. XXVII. Derivatives of 1-tosyl-L-3-aminopyrrolid-2-one: Preparation and synthetic potentialities
    1959, Vol. 24, Issue 10, pp. 3449–3467 [Abstract]
  • J. Rudinger, K. Poduška, M. Zaoral and K. Jošt
    Amino-acids and peptides. XXVI. An improved synthesis of L-glutamine
    1959, Vol. 24, Issue 6, pp. 2013–2017 [Abstract]
  • M. Zaoral and J. Rudinger
    Amino-acids and peptides. XXV. Dehydration of derivatives of asparagine and glutamine; A new route to α,γ-diaminobutyric acid, ornithine, and arginine
    1959, Vol. 24, Issue 6, pp. 1993–2012 [Abstract]
  • M. Zaoral
    Amino acids and peptides. XXIV. Preparation of DL-α,γ-diaminobutyric acid and its derivatives from γ-butyrolactone
    1959, Vol. 24, Issue 4, pp. 1314–1319 [Abstract]
  • J. Rudinger and Z. Pravda
    Amino-acids and peptides. XXII. Synthesis of some glutamine peptides; The structure of eisenin
    1958, Vol. 23, Issue 10, pp. 1947–1957 [Abstract]
  • K. Poduška and J. Rudinger
    Amino-acids and peptides. XXI. N-Substituted pyrrolidones as intermediates in the synthesis of γ-aminobutyric and α,γ-diaminobutyric acid peptides
    1957, Vol. 22, Issue 4, pp. 1283–1292 [Abstract]
  • J. Rudinger, J. Honzl and M. Zaoral
    Syntheses in the oxytocin field. IV. Two analogues
    1956, Vol. 21, Issue 3, pp. 770–772 [Abstract]
  • J. Rudinger, J. Honzl and M. Zaoral
    Synthetic studies in the oxytocin field. III. An alternative synthesis of oxytocin
    1956, Vol. 21, Issue 1, pp. 202–210 [Abstract]
  • J. Honzl and J. Rudinger
    Synthetic studies in the oxytocin field. II. The synthesis of some derivatives of L-cysteinyl-L-tyrosylglycine, L-cysteinyl-L-tyrosyl-L-leucine and L-cysteinyl-L-tyrosyl-L-isoleucine
    1955, Vol. 20, Issue 5, pp. 1190–1198 [Abstract]
  • K. Poduška, J. Rudinger and F. Šorm
    Amino-acids and peptides. XVI. Peptides of DL-α,β-diaminopropionic acid
    1955, Vol. 20, Issue 5, pp. 1174–1182 [Abstract]
  • Z. Pravda and J. Rudinger
    Amino-acids and peptides. XIII. A synthesis of L-proline from L-glutamic acid
    1955, Vol. 20, Issue 1, pp. 1–8 [Abstract]
  • J. Rudinger and H. Czurbová
    Amino-acids and peptides. XII. A new resolution of DL-glutamic acid; Synthesis of D-glutamine and γ-D-glutamylglycine
    1954, Vol. 19, Issue 2, pp. 386–392 [Abstract]
  • J. Rudinger
    Amino-acids and peptides. XI. A new synthesis of peptides of glutamic acid
    1954, Vol. 19, Issue 2, pp. 375–385 [Abstract]
  • J. Rudinger
    Amino-acids and peptides. X. Some derivatives and reactions of 1-p-toluenesulphonyl-L-pyrrolid-5-one-2-carboxylic acid
    1954, Vol. 19, Issue 2, pp. 365–374 [Abstract]
  • M. Zaoral, J. Rudinger and F. Šorm
    Amino acids and peptides. VIII. Peptides of α,γ-diaminobutyric acid
    1953, Vol. 18, Issue 4, pp. 530–549 [Abstract]
  • J. Sicher, M. Svoboda, M. Hrdá, J. Rudinger and F. Šorm
    Studies in the chloramphenicol series. VI. Steric course of the reduction of dehydrochloramphenicol and related compounds
    1953, Vol. 18, Issue 4, pp. 487–499 [Abstract]
  • V. Herout, M. Zaoral and F. Šorm
    On terpenes. XXXIX. Synthesis of two tetrahydrobisabolols
    1953, Vol. 18, Issue 1, pp. 122–126 [Abstract]
  • F. Šorm, M. Zaoral and V. Herout
    On terpenes. XXXVIII. On the constitution of natural bisabolol and bisabolol monoxide from Matricaria oil
    1953, Vol. 18, Issue 1, pp. 116–121 [Abstract]
  • F. Šorm, M. Zaoral and V. Herout
    On terpenes. XXXI. On the composition of the oil of Matricaria chamomilla L.
    1951, Vol. 16, pp. 626–638 [Abstract]
  • J. Rudinger
    Preparative separation of the isomeric half-esters of carbobenzoxyglutamic acid by countercurrent distribution
    1951, Vol. 16, pp. 615–619 [Abstract]
  • J. Rudinger and F. Šorm
    On proteins and amino-acids. VIII. A new synthesis of glutathione
    1951, Vol. 16, pp. 214–220 [Abstract]
  • F. Šorm, M. Zaoral, J. Arient, J. Plíva and V. Herout
    On terpenes. XXIII. On the composition of oil of carrot (Daucus carrota L.)
    1951, Vol. 16, pp. 47–56 [Abstract]
  • F. Šorm and J. Rudinger
    On proteins and amino-acids III. The synthesis of γ-L-glutamyl-L-tyrosine
    1950, Vol. 15, pp. 491–500 [Abstract]