Solid-phase synthesis of [8-arginine]-vasopressin through a crystalline protected nonapeptide intermediate and biological properties of the hormone

A series of solid-phase syntheses of the protected precursor II of DDAVP was carried out. Experimental conditions were developed under which practically pure II can reproducibly be obtained in yields better than 60%. The protected precursors of DDAVP obtained by liquid- and solid-phase synthesis and DDAVP samples obtained from these precursors were undistinguishable by conventional analytical or pharmacological assays.

Download Full-text

Solid Phase Synthesis of Novel Fullerene Nucleotides Conjugates

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.266.200 ◽

2011 ◽

Vol 266 ◽

pp. 200-203

Author(s):

Jing Zhang ◽

Ya Dong Zhang

Keyword(s):

Aspartic Acid ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Biological Properties ◽

Azomethine Ylide ◽

Hydroxyl Group ◽

Spectrometric Analysis ◽

Phase Synthesis ◽

Chemical Structures ◽

Controlled Pore Glass

N-substituted 3, 4-fullero pyrrolidine was synthesized according to 1, 3-dipolar cycloaddition of the azomethine ylide. Aspartic acid with protected α-amino and α-carboxyl groups was reacted with the activated hydroxyl group of N-substituted 3, 4-fullero pyrrolidine. The products were deprotected, affording the monofullerene aspartic acid (mFas). The conjugate FasT was synthesized by reaction of mFas containing protected amino group with the thymidylic acid derivatived controlled pore glass (CPG) using solid phase synthesis. All of the above fullerene derivatives were characterized by UV–vis, 1H NMR, IR and MS spectrometric analysis, giving the correct spectra with regard to their chemical structure. The chemical structures of fullerene nucleotides conjugate FasT is different from previous reports and may have novel biological properties. Moreover, they are more suitable for applications in biomedical research due to their solubilization in THF and DMSO. They have a potential to be used as monomer for the automatic synthesis. It allows further conjugation with specific biomolecules including amino acids, peptides, nucleotides and nucleic acids. A novel method has been developed to synthesize fullerene nucleotides conjugate. Their unique chemical structures make them very interesting for their potential use in medicine and biology.

Download Full-text

[MeArg1, NLe10]-apelin-12: Optimization of solid-phase synthesis and evaluation of biological properties in vitro and in vivo

Peptides ◽

10.1016/j.peptides.2020.170320 ◽

2020 ◽

Vol 129 ◽

pp. 170320 ◽

Cited By ~ 1

Author(s):

Maria Sidorova ◽

Irina Studneva ◽

Valery Bushuev ◽

Marina Pal’keeva ◽

Alexander Molokoedov ◽

...

Keyword(s):

Solid Phase Synthesis ◽

Solid Phase ◽

Biological Properties ◽

Phase Synthesis

Download Full-text

Simple Solid-Phase Synthesis and Biological Properties of Carbohydrate−Oligonucleotide Conjugates Modified at the 3′-Terminus

Bioconjugate Chemistry ◽

10.1021/bc100205v ◽

2010 ◽

Vol 21 (9) ◽

pp. 1685-1690 ◽

Cited By ~ 12

Author(s):

Yutaka Ikeda ◽

Daisuke Kubota ◽

Yukio Nagasaki

Keyword(s):

Solid Phase Synthesis ◽

Solid Phase ◽

Biological Properties ◽

Phase Synthesis ◽

Oligonucleotide Conjugates

Download Full-text

Synthesis and biological properties of vasopressin analogues containing 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Collection of Czechoslovak Chemical Communications ◽

10.1135/cccc19901099 ◽

1990 ◽

Vol 55 (4) ◽

pp. 1099-1105 ◽

Cited By ~ 6

Author(s):

Zdenko Procházka ◽

Juris E. Ancans ◽

Jiřina Slaninová ◽

Alena Machová ◽

Tomislav Barth ◽

...

Keyword(s):

Amino Acid ◽

Carboxylic Acid ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Biological Activities ◽

Biological Properties ◽

Phase Synthesis ◽

Aromatic Residues ◽

Synthesis Methodology ◽

Vasopressin Analogues

Solid phase synthesis methodology on a benzhydrylamine resin was used for the synthesis of three analogues of vasopressin with the non-coded amino acid, 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (Tic), in the position 2 ([Tic2, Lys8]VP (I)) and in the position 3 ([Tic3, Lys8]VP (II)). The analogue containing only one Tic in place of both aromatic residues was also isolated (des-Tyr2-[Tic3, Lys8]VP (III)). The biological activities of all analogues were negligible.

Download Full-text