scholarly journals Liquid Phase Peptide Synthesis by the Fragment Condensation on Soluble Polymer Support. I. Efficient Coupling and Relative Reactivity of a Peptide Fragment with Various Coupling Reagents

1978 ◽  
Vol 51 (5) ◽  
pp. 1477-1480 ◽  
Author(s):  
Mitsuaki Narita
Keyword(s):  
Liquid Phase ◽  
Peptide Synthesis ◽  
Relative Reactivity ◽  
Polymer Support ◽  
Peptide Fragment ◽  
Coupling Reagents ◽  
Soluble Polymer ◽  
Efficient Coupling ◽  
Fragment Condensation

Ynamide: A New Coupling Reagent for Amide and Peptide Synthesis

Synlett ◽  
2017 ◽  
Vol 28 (14) ◽  
pp. 1663-1670 ◽  
Author(s):  
Long Hu ◽  
Junfeng Zhao
Keyword(s):  
Peptide Synthesis ◽  
Phosphonium Salt ◽  
Peptide Fragment ◽  
Coupling Reagents ◽  
Development History ◽  
Coupling Reagent ◽  
History Of ◽  
Fragment Condensation ◽  
Carbodiimide Coupling ◽  
Guanidinium Salt

The discovery and application of ynamide coupling reagents is highlighted with a brief summary of the development history of coupling reagents in amide and peptide synthesis. As novel coupling reagents, ynamides are not only effective for simple amide and dipeptide synthesis but also can be used for peptide fragment condensation. More importantly, no racemization was detected during the activation of α-chiral carboxylic acids by employing ynamide coupling reagents.1 Introduction2 Carbodiimide Coupling Reagents3 Uronium/Guanidinium Salt Coupling Reagents4 Phosphonium Salt Coupling Reagents5 Ethoxyacetylene as a Coupling Reagent6 Ynamine Coupling Reagents7 Ynamide Coupling Reagents8 Summary and Outlook

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.

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