An improved soluble polynorbornene support for peptide synthesis

RSC Advances ◽  
2015 ◽  
Vol 5 (113) ◽  
pp. 93027-93031
Author(s):  
Nimmashetti Naganna ◽  
Nandita Madhavan
Keyword(s):  
Peptide Synthesis ◽  
Side Chains ◽  
Coupling Reagents

A soluble polynorbornene support containing an oligoether linker as well as alkyl and oligoether side chains has been developed and used to synthesize Leu5-Enkephalin in 52% overall yield using only 1.2 equivalents of coupling reagents.

A Strategy for Thioamide Incorporation During Fmoc Solid-Phase Peptide Synthesis with Robust Stereochemical Integrity

2019 ◽  
Author(s):  
luis camacho III ◽  
Bryan J. Lampkin ◽  
Brett VanVeller
Keyword(s):  
Amino Acid ◽  
Functional Groups ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Side Chains ◽  
Amino Acid Side Chains ◽  
Peptide Elongation

We describe a method to protect the sensitive stereochemistry of the thioamide—in analogy to the protection of the functional groups of amino acid side chains—in order to preserve the thioamide moiety during peptide elongation.<br>

ChemInform Abstract: Sulfonates of N-Triazinylammonium Salts as Highly Efficient, Inexpensive and Environmentally Friendly Coupling Reagents for Peptide Synthesis

ChemInform ◽  
2008 ◽  
Vol 39 (28) ◽  
Author(s):  
Beata Kolesinska ◽  
Justyna Fraczyk ◽  
Giuseppina Sabatino ◽  
Anna M. Papini ◽  
Zbigniew J. Kaminski
Keyword(s):  
Peptide Synthesis ◽  
Environmentally Friendly ◽  
Coupling Reagents ◽  
Highly Efficient

Synthetic hydroxymethyl-porphyrins for protection of carboxy group

2007 ◽  
Vol 11 (06) ◽  
pp. 434-441 ◽  
Author(s):  
Hitoshi Tamiaki ◽  
Kouji Kumon ◽  
Reiko Shibata
Keyword(s):  
Liquid Phase ◽  
Carboxylic Acid ◽  
Thin Layer ◽  
Peptide Synthesis ◽  
Phenyl Group ◽  
Coupling Reagents ◽  
Protective Groups ◽  
Simple Filtration ◽  
Meso Position ◽  
Layer Chromatography

Hydroxymethyl-porphyrins were prepared by modifying tetraarylporphyrin possessing a p-(methoxycarbonyl)phenyl group at the meso-position and octaethylporphyrin. The synthetic alcohols reacted with carboxylic acids by the use of coupling reagents, to give the corresponding esters quantitatively. Due to the porphyrin dye moiety, the esterification was easily monitored on thin layer chromatography, and the resulting esters were highly soluble in most organic solvents and easily handled. The esters were readily cleaved by the action of an acid to give the original carboxylic acid and hydroxymethyl-porphyrin. Separation of the two species was performed by simple filtration: the carboxylic acid was soluble (filtrate) and the porphyrins were precipitates in methanol. These protective groups for carboxy groups were useful for peptide synthesis in the liquid phase.

Azabenzotriazole (HOAt) derivatives as superior coupling reagents for peptide synthesis

Peptides 1994 ◽  
1995 ◽  
pp. 23-25 ◽  
Author(s):  
F. Albericio ◽  
I. Abdelmoty ◽  
J. M. Bofill ◽  
L. A. Carpino ◽  
A. El-Faham ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Coupling Reagents

In-Peptide Synthesis of Imidazolidin-2-one Scaffolds, Equippable with Proteinogenic or Taggable/Linkable Side Chains, General Promoters of Unusual Secondary Structures

2019 ◽  
Vol 84 (9) ◽  
pp. 4992-5004 ◽  
Author(s):  
Rossella De Marco ◽  
Junwei Zhao ◽  
Arianna Greco ◽  
Simone Ioannone ◽  
Luca Gentilucci
Keyword(s):  
Peptide Synthesis ◽  
Secondary Structures ◽  
Side Chains

N-Methylamino Acids in Peptide Synthesis. II. A New Synthesis of N-Benzyloxycarbonyl, N-Methylamino Acids

1973 ◽  
Vol 51 (12) ◽  
pp. 1915-1919 ◽  
Author(s):  
John R. McDermott ◽  
N. Leo Benoiton
Keyword(s):  
Amino Acids ◽  
Methyl Iodide ◽  
Peptide Synthesis ◽  
Side Chains ◽  
Butyl Group ◽  
New Synthesis ◽  
Derivatives Of

Reaction of N-benzyloxycarbonyl derivatives of aliphatic amino acids, and threonine, aspartic, and glutamic acids whose side-chains were protected with the t-butyl group, gave the corresponding N-methylamino acid derivatives in good yields. The methionine derivative could be obtained by using only one mol of methyl iodide. Derivatives of threonine, and aspartic and glutamic acids whose side-chains were not protected could not be methylated. Analysis of the crude products of methylation in three cases showed that they contained 0–1% of racemized material.

Ynamides as Racemization-Free Coupling Reagents for Amide and Peptide Synthesis

2016 ◽  
Vol 138 (40) ◽  
pp. 13135-13138 ◽  
Author(s):  
Long Hu ◽  
Silin Xu ◽  
Zhenguang Zhao ◽  
Yang Yang ◽  
Zhiyuan Peng ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Coupling Reagents ◽  
Racemization Free Coupling

Total Synthesis of Dehydrodidemnin B. Use of Uronium and Phosphonium Salt Coupling Reagents in Peptide Synthesis in Solution†

1997 ◽  
Vol 62 (2) ◽  
pp. 354-366 ◽  
Author(s):  
Gemma Jou ◽  
Isabel González ◽  
Fernando Albericio ◽  
Paul Lloyd-Williams ◽  
Ernest Giralt
Keyword(s):  
Total Synthesis ◽  
Peptide Synthesis ◽  
Phosphonium Salt ◽  
Coupling Reagents

Benzyloxy Derivatives of Triazine-based Coupling Reagents Designed for an Efficient Solid Phase Peptide Synthesis on Polystyrene Resin

2007 ◽  
Vol 13 (1-2) ◽  
pp. 229-236 ◽  
Author(s):  
Konrad Jastrząbek ◽  
Beata Kolesińska ◽  
Giuseppina Sabatino ◽  
Fabio Rizzolo ◽  
Anna M. Papini ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Coupling Reagents ◽  
Polystyrene Resin ◽  
Derivatives Of
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