Vasopressin analogs modified in position 3. Influence of changes of configuration

1979 ◽  
Vol 44 (10) ◽  
pp. 3128-3132 ◽  
Author(s):  
Milan Zaoral ◽  
Danuta Konopinska ◽  
Ivan Bláha ◽  
Viktor Krchňák ◽  
Jana Škopková ◽  
...  
Keyword(s):  
Methyl Ester ◽  
Disulfide Bridge ◽  
Protecting Groups ◽  
Diaminobutyric Acid ◽  
Antidiuretic Effect ◽  
Phenylalanine Methyl Ester

The condensation of p-toluenesulfonyl-S-benzylcysteinyl-tyrosine azide with D-phenylalanine methyl ester afforded p-toluenesulfonyl-S-benzylcysteinyl-tyrosyl-D-phenylalanine methyl ester which was subsequently converted into the hydrazide and azide and coupled with glutaminyl-asparaginyl-S-benzylcysteine methyl ester. p-Toluenesulfonyl-S-benzylcysteinyl-tyrosyl-D-phenylalanyl-glutaminyl-asparaginyl-S-benzylcysteine methyl ester was condensed via the hydrazide and azide with prolyl-Nγ-p-toluenesulfonyl-αγ-diaminobutyryl-glycine amide. After removal of the protecting groups, closure of the disulfide bridge and purification, [3-D-phenylalanine, 8-α,γ-diaminobutyric acid]vasopressin was obtained which shows an appreciable antidiuretic effect of distinct specifity.

[1-β-Mercaptopropionic acid, 8-norarginine]vasopressin and [1-β-mercaptopropionic acid, 8-D-norarginine]vasopressin. Two analogs with strong biological effects

1979 ◽  
Vol 44 (4) ◽  
pp. 1179-1186 ◽  
Author(s):  
Milan Zaoral ◽  
František Brtník ◽  
Martin Flegel ◽  
Tomislav Barth ◽  
Alena Machová
Keyword(s):  
Biological Effects ◽  
Disulfide Bridge ◽  
Protecting Groups ◽  
Pressor Effect ◽  
Amino Groups ◽  
Mercaptopropionic Acid ◽  
Antidiuretic Effect ◽  
Carbodiimide Method

[1-β-Mercaptopropionic acid, 8-norarginine]vasopressin (L8, D8; I, II) was prepared by condensation of β-benzylthiopropionyl-tyrosyl-phenylalanyl-glutaminyl-asparaginyl-S-benzylcysteine with Nγ-benzyloxycarbonyl-α,γ-diaminobutyryl-glycine amide (L2, D2) by the azide or carbodiimide method, respectively, removal of the benzyloxycarbonyl residue, guanidination of γ-amino groups, removal of protecting groups, closing of the disulfide bridge, and electrophoretic purification. I has an almost 2 times higher antidiuretic effect than DDAVP and a 3 times higher pressor effect than AVP. II has 20-25% of the antidiuretic effect of DDAVP and 16 IU/mg of the pressor effect.

ChemInform Abstract: THE SYNTHESIS OF A SWEET PEPTIDE, ALPHA-L-ASPARTYL-L-PHENYLALANINE METHYL ESTER, WITHOUT THE USE OF PROTECTING GROUPS

1973 ◽  
Vol 4 (36) ◽  
pp. no-no
Author(s):  
YASUO ARIYOSHI ◽  
TETSUO YAMATANI ◽  
NOBORU UCHIYAMA ◽  
YOHKO ADACHI ◽  
NAOTAKE SATO
Keyword(s):  
Methyl Ester ◽  
Protecting Groups ◽  
Phenylalanine Methyl Ester

scholarly journals The Synthesis of a Sweet Peptide, α-L-Aspartyl-L-phenylalanine Methyl Ester, without the Use of Protecting Groups

1973 ◽  
Vol 46 (6) ◽  
pp. 1893-1895 ◽  
Author(s):  
Yasuo Ariyoshi ◽  
Tetsuo Yamatani ◽  
Noboru Uchiyama ◽  
Yohko Adachi ◽  
Naotake Sato
Keyword(s):  
Methyl Ester ◽  
Protecting Groups ◽  
Phenylalanine Methyl Ester

Vasopressin and oxytocin analogs with interchanged sequence of amino acids in positions 7 and 8. synthesis and biological effects

1981 ◽  
Vol 46 (9) ◽  
pp. 2136-2139 ◽  
Author(s):  
Ivo Bláha ◽  
Viktor Krchňák ◽  
Milan Zaoral
Keyword(s):  
Amino Acids ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Biological Effects ◽  
Free Flow ◽  
Protecting Groups ◽  
Pressor Effect ◽  
Phase Synthesis ◽  
Antidiuretic Effect

p-Toluenesulfonyl-S-benzylcysteinyl-tyrosyl-phenylalanyl-glutaminyl-asparaginyl-S-benzylcysteinyl-NG-p-toluenesulfanylarginyl-prolyl-glycineamide (I) and S-benzylcysteinyl-tyrosyl-isoleucyl-glutaminyl-asparaginyl-S-benzylcysteinyl-leucyl-prolyl-glycine amide (III) were prepared by solid phase synthesis. After removal of the protecting groups, closure of the disulfide ring, and purification by continuous free-flow electrophoresis [arginine7, proline8]vasopressin (II) and [leucine7, proline8]oxytocin (IV) were obtained. The antidiuretic effect of II is markedly higher than its pressor effect; IV possesses c. 6% of the uterotonic and c. 10% of the galactogogous effect of oxytocin.

Effects of the preparation method on the performance of the Cu/ZnO/Al2O3 catalyst for the manufacture of l-phenylalaninol with high ee selectivity from l-phenylalanine methyl ester

2014 ◽  
Vol 4 (4) ◽  
pp. 1132-1143 ◽  
Author(s):  
Zhangping Shi ◽  
Xiuzhen Xiao ◽  
Dongsen Mao ◽  
Guanzhong Lu
Keyword(s):  
Methyl Ester ◽  
Catalytic Hydrogenation ◽  
Preparation Method ◽  
Phenylalanine Methyl Ester ◽  
Al2o3 Catalyst

Efficient catalytic hydrogenation of l-phenylalanine methyl ester to l-phenylalaninol over the Cu/ZnO/Al2O3 catalyst with ~100% ee selectivity.

scholarly journals 4-fluorobenzylamine and phenylalanine methyl ester conjugates OF 2-nitroimidazole: Evaluation as hypoxic cell radiosensitizers

1992 ◽  
Vol 22 (3) ◽  
pp. 593-596 ◽  
Author(s):  
Pradeep K. Arg ◽  
Sudha Garg ◽  
William G. Degraff ◽  
Michael R. Zalutsky ◽  
James B. Mitchell
Keyword(s):  
Methyl Ester ◽  
Hypoxic Cell ◽  
Phenylalanine Methyl Ester

Synthesis of aspartame via asymmetric hydrogenation of N-protected (Z)-N-.alpha.-L-aspartyl-.DELTA.-phenylalanine methyl ester

1986 ◽  
Vol 51 (7) ◽  
pp. 1126-1128 ◽  
Author(s):  
Claudio Fuganti ◽  
Piero Grasselli ◽  
Luciana Malpezzi ◽  
Paolo Casati
Keyword(s):  
Methyl Ester ◽  
Asymmetric Hydrogenation ◽  
Phenylalanine Methyl Ester
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