Synthesis of oxytocin, arginine-vasopressin and its deamino-analogue using 2,4,6-trimethylbenzyl group for protection of the cysteine sulfur

1981 ◽  
Vol 46 (1) ◽  
pp. 286-299 ◽  
Author(s):  
František Brtník ◽  
Milan Krojidlo ◽  
Tomislav Barth ◽  
Karel Jošt
Keyword(s):  
Peptide Synthesis ◽  
Hydrogen Fluoride ◽  
Sulfur Atom ◽  
Arginine Vasopressin ◽  
Liquid Hydrogen ◽  
Trifluoromethanesulfonic Acid ◽  
Protecting Groups ◽  
Mild Conditions

Preparation of oxytocin, arginine-vasopressin and its deamino-analogue serves as an example of use of 2,4,6-trimethylbenzyl group for protection of the cysteine sulfur atom in the peptide synthesis. This modified benzyl group is sufficiently stable under conditions of solvolytic removal of common amino-protecting groups and it can be cleaved off under mild conditions with liquid hydrogen fluoride or trifluoromethanesulfonic acid.

[1-β-Mercaptopropionic acid, 8-α-amino-β-guanidinopropionic acid]vasopressin and [1-β-mercaptopropionic acid, 8-D-α-amino-β-guanidinopropionic acid]vasopressin; Analogs showing a high and specific antidiuretic effect

1979 ◽  
Vol 44 (8) ◽  
pp. 2447-2450 ◽  
Author(s):  
Milan Zaoral ◽  
Viktor Krchňák ◽  
František Brtník ◽  
Alena Machová ◽  
Jana Škopková
Keyword(s):  
Hydrogen Fluoride ◽  
Arginine Vasopressin ◽  
Liquid Hydrogen ◽  
Protecting Groups ◽  
Pressor Effect ◽  
Mercaptopropionic Acid ◽  
Antidiuretic Effect

β-Benzylthiopropionyl-tyrosyl-phenylalanyl-glutaminyl-asparaginyl-S-benzylcysteine azide was condensed with prolyl-α-amino-nitroguanidinopropionyl-glycine amides (L2; D2) to β-benzylthiopropionyl-tyrosyl-phenylalanyl-glutaminyl-asparaginyl-S-benzylcysteinyl-prolyl-α-amino-β-nitroguanidinopropionyl-glycine amides (L8; D8) which after removal of the protecting groups in liquid hydrogen fluoride, closure of the disulfide ring, desalting, and electrophoretic purification afforded [1-β-mercaptopropionic acid, 8-α-amino-β-guanidinopropionic acid]vasopressin (I) and [1-β-mercaptopropionic acid, 8-D-α-amino-β-guanidinopropionic acid]vasopressin (II). The antidiuretic effect of I (II) is about 10% of the effect of [1-β-mercaptopropionic acid, 8-D-arginine]vasopressin (DDAVP) (87 ± 8% DDAVP), the pressor effect is 49.5 I.U./mg (2.7 I.U./mg).

Obviation of hydrogen fluoride in Boc chemistry solid phase peptide synthesis of peptide-αthioesters

2016 ◽  
Vol 52 (97) ◽  
pp. 13979-13982 ◽  
Author(s):  
Zachary P. Gates ◽  
Balamurugan Dhayalan ◽  
Stephen B. H. Kent
Keyword(s):  
Peptide Synthesis ◽  
Hydrogen Fluoride ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Trifluoromethanesulfonic Acid

Trifluoromethanesulfonic acid performs comparably to hydrogen fluoride for the on-resin global deprotection of peptides prepared by Boc chemistry solid phase peptide synthesis.

Synthesis of four new V1 antagonists of arginine-vasopressin (AVP) containing new thioacids at position 1 and their vasoconstrictor activity towards isolated mesenteric arterial vessels of rats

1991 ◽  
Vol 56 (2) ◽  
pp. 491-498 ◽  
Author(s):  
Bernard Lammek ◽  
Izabela Derdowska ◽  
Tomasz M. Wierzba ◽  
Witold Juzwa
Keyword(s):  
Peptide Synthesis ◽  
Arginine Vasopressin ◽  
Solid Phase ◽  
Structural Features ◽  
Phase Method ◽  
Competitive Antagonist ◽  
Vasoconstrictor Effect ◽  
Solid Phase Method

In an attempt to determine some of the structural features in position 1 that account for V1 antagonism, four new analogues of arginine-vasopressin were synthesized and the effect of the modifications on the vasoconstrictor activity was checked using isolated mesenteric arterial vessels of rats. The protected precursors required for these analogues were synthesized by a solid phase method of peptide synthesis. One of the reported analogues, namely [1-(4-mercapto-4-tetrahydrothiopyraneacetic acid)., 2-O-methyltyrosine, 8-arginine]vasopressin appears to be a potent competitive antagonist of the vasoconstrictor effect by AVP.

Selective acid hydrolysis of 2,4,6-trimethylbenzyl esters and its application in peptide synthesis

1966 ◽  
Vol 19 (8) ◽  
pp. 1511 ◽  
Author(s):  
FHC Stewart
Keyword(s):  
Acid Hydrolysis ◽  
Peptide Synthesis ◽  
Trifluoroacetic Acid ◽  
Ester Group ◽  
Protecting Groups ◽  
Alkaline Conditions ◽  
Hydrolysis Of

Experiments with various N-acylamino acid 2,4,6-trimethylbenzyl esters have shown that the ester group is cleaved selectively by cold trifluoroacetic acid without affecting benzyloxycarbonyl, formyl, or phthaloyl amino-protecting groups present. The possible value of this selective behaviour in peptide syntheses where the use of alkaline conditions would be detrimental is illustrated by the synthesis of certain dipeptide derivatives.

Sign in / Sign up

Export Citation Format

Share Document