scholarly journals Amino Acids and Peptides. LIV. Application of 2-Adamantyl Derivatives as Protecting Groups to the Synthesis of Peptide Fragments Related to Sulfolobus solifataricus Ribnuclease. I.

1999 ◽  
Vol 47 (8) ◽  
pp. 1089-1096 ◽  
Author(s):  
Yoshio OKADA ◽  
Shima JOSHI ◽  
Noriyuki SHINTOMI ◽  
Yukihiro KONDO ◽  
Yuko TSUDA ◽  
...  
Keyword(s):  
Amino Acids ◽  
Protecting Groups ◽  
Peptide Fragments

scholarly journals Amino Acids and Peptides. LV. Application of 2-Adamantyl Derivatives as Protecting Groups to the Synthesis of Peptide Fragments Related to Sulfolobus sollfataricus Ribnuclease. II.

1999 ◽  
Vol 47 (8) ◽  
pp. 1097-1101 ◽  
Author(s):  
Yuko TSUDA ◽  
Shima JOSHI ◽  
Noriyuki SHINTOMI ◽  
Yukihiro KONDO ◽  
Kazuko OHGI ◽  
...  
Keyword(s):  
Amino Acids ◽  
Protecting Groups ◽  
Peptide Fragments

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.

scholarly journals Epimerization-free C-term Activation of Peptide Fragments by Ball-Milling

2020 ◽  
Author(s):  
Yves Yeboue ◽  
Marion Jean ◽  
Gilles Subra ◽  
Jean Martinez ◽  
Frédéric Lamaty ◽  
...  
Keyword(s):  
Amino Acids ◽  
Ball Milling ◽  
High Yield ◽  
Coupling Agents ◽  
Peptide Fragment ◽  
Peptide Fragments ◽  
Solution Synthesis ◽  
High Yields ◽  
Synthesis Approach ◽  
Yield And Purity

Ball-milling enabled to perform [2+1], [2+2], and [2+3] peptide couplings with high yields and, if any, very low epimerization. Very good results were obtained with peptide fragments containing highly epimerization-prone and/or highly hindered amino acids at C-term such as phenylglycine, cysteine and valine. Ball-milling was clearly identified as the key element to obtain both high yield and purity along with low epimerization. Indeed, the ball-milling conditions proved to be superior to the classical solution synthesis approach on a various array of widely used coupling agents. These results open avenues for the development of highly efficient, convergent and flexible peptide synthesis strategies based on peptide fragment couplings mediated by ball-milling.

scholarly journals Epimerization-free C-term Activation of Peptide Fragments by Ball-Milling

2020 ◽  
Author(s):  
Yves Yeboue ◽  
Marion Jean ◽  
Gilles Subra ◽  
Jean Martinez ◽  
Frédéric Lamaty ◽  
...  
Keyword(s):  
Amino Acids ◽  
Ball Milling ◽  
High Yield ◽  
Coupling Agents ◽  
Peptide Fragment ◽  
Peptide Fragments ◽  
Solution Synthesis ◽  
High Yields ◽  
Synthesis Approach ◽  
Yield And Purity

Ball-milling enabled to perform [2+1], [2+2], and [2+3] peptide couplings with high yields and, if any, very low epimerization. Very good results were obtained with peptide fragments containing highly epimerization-prone and/or highly hindered amino acids at C-term such as phenylglycine, cysteine and valine. Ball-milling was clearly identified as the key element to obtain both high yield and purity along with low epimerization. Indeed, the ball-milling conditions proved to be superior to the classical solution synthesis approach on a various array of widely used coupling agents. These results open avenues for the development of highly efficient, convergent and flexible peptide synthesis strategies based on peptide fragment couplings mediated by ball-milling.

Effect of Pharmaceutical Bone Growth Stimulation With Novel Anabolic Peptides: Biomechanical and Bone Density Measurements in a Rat Model

2003 ◽  
Author(s):  
Michael J. Askew ◽  
Gary B. Schneider ◽  
Kristina J. Grecco ◽  
Jason Hsu ◽  
Emily Mugler ◽  
...  
Keyword(s):  
Amino Acids ◽  
Side Effects ◽  
Bone Density ◽  
Bone Growth ◽  
Growth Stimulation ◽  
Growth Hormones ◽  
Peptide Fragments ◽  
Cross Sectional ◽  
Adverse Side Effects ◽  
Bending Modulus

Pharmaceutical bone growth stimulation holds promise for prevention and treatment bone disorders, and the enhancement of fracture healing. Bone growth hormones have begun to have limited clinical use, but can illicit adverse side effects. Recent studies have shown that short peptides (less than 15 amino acids) derived from the protein sequence of Vitamin D Binding Protein (DBP), can enhance bone formation (osteogenesis). These peptides may have potential as controllable bone growth stimulators without the adverse side effects and cost of bone growth hormones. Rats, injected every other day for two weeks with DBP-based peptide fragments ranging from 3 to 13 amino acids in length, were euthanized and the tibias and femurs were scanned by peripheral quantitative computerized tomography (pQCT) to determine bone density and cross-sectional geometric properties. The bones were then tested in three-point bending to determine strength and bending modulus. Injection of DBP-based peptides over only a 2-week period resulted in significant (p<0.05) increases in bone density and material properties in the experimental rat bones in comparison to controls injected with saline. The short length of these effective peptides suggests their use not only in systemic injections but also as clinically convenient pills taken orally for pharmaceutically induced bone growth stimulation.

Structure-function relationships of peptide fragments of gastrin and cholecystokinin.

1977 ◽  
Vol 233 (4) ◽  
pp. E286
Author(s):  
D L Kaminski ◽  
M J Ruwart ◽  
M Jellinek
Keyword(s):  
Amino Acids ◽  
Structure Function ◽  
Bile Flow ◽  
Hydrogen Ion ◽  
Biliary System ◽  
Peptide Fragments ◽  
Hepatic Bile ◽  
Amino Acid Peptide ◽  
The Common ◽  
Active Fragments

This study evaluates the structure-function relationships of the C-terminal peptide fragments of gastrin and cholecystokinin (CCK) in the biliary system and the stomach. Dogs with chronic biliary and gastric fistulas were used. Administration of the common fragments of CCK and gastrin with four and five amino acids and the active fragments of CCK with six through eight amino acids without sulfation of tyrosine in position 7 failed to alter hepatic bile flow from control values while significantly stimulating gastric hydrogen ion output. Administration of the seven and eight amino acid peptide fragments of CCK with sulfation of tyrosine in position 7 significantly increased hepatic bile flow. Administration of the sulfated octapeptide with 4 microgram/kg per h of nonsulfated octapeptide did not result in the inhibition of the choleresis produced by the sulfated peptide. The gastric hydrogen ion response produced by the administration of the nonsulfated and sulfated peptide was equal to that of the nonsulfated peptide alone. These results suggest that in the biliary system the receptor is highly specific as sulfation of the peptide fragment of CCK is essential for combining with the receptor, whereas in the stomach the receptor has little specificity and combines with all of the peptide fragments evaluated.

Synthese von immobilisierten Peptidfragmenten an Polystyrol-Polyoxyethylen zur Affinitätschromatographie /Synthesis of Immobilized Peptide Fragments on Polystyrene-Polyoxyethylene for Affinity Chromatography

1987 ◽  
Vol 42 (4) ◽  
pp. 455-460 ◽  
Author(s):  
Ernst Bayer ◽  
Heribert Hellstern ◽  
Heiner Eckstein
Keyword(s):  
Affinity Chromatography ◽  
Organic Solvents ◽  
Peptide Synthesis ◽  
Stationary Phases ◽  
Peptide Bond ◽  
Protecting Groups ◽  
Peptide Fragments ◽  
Solid Supports ◽  
Polystyrene Beads ◽  
Acidic Conditions

Abstract Polystyrene-polyoxyethylene craft copolymers have been used for step-wise peptide synthesis. After completion of synthesis the protecting groups are cleaved under acidic conditions, where the polymer-peptide bond is stable. These gels in comparison to polystyrene peptide gels, show better properties for applications in affinity chromatography as well as synthesis on solid supports, because the advantageous properties of polystyrene beads are combined with the excellent spacer behavior of polyoxyethylene chains (mobility, solvation by water and organic solvents). Peptide gels with polylysine sequences have been synthesized as highly selective stationary phases for the separation of the homologous oligo desoxyribonucleotides (dT)n with n = 1-3. The principal possibilities of these gels for affinity chromatography is demonstrated.

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