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

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

ChemInform ◽  
2010 ◽  
Vol 28 (20) ◽  
pp. no-no ◽  
Author(s):  
G. JOU ◽  
I. GONZALEZ ◽  
F. ALBERICIO ◽  
P. LLOYD-WILLIAMS ◽  
E. GIRALT
Keyword(s):  
Total Synthesis ◽  
Peptide Synthesis ◽  
Phosphonium Salt ◽  
Coupling Reagents

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

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.

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

Pyrrolidide formation as a side reaction during activation of carboxylic acids by phosphonium salt coupling reagents

1999 ◽  
Vol 6 (4) ◽  
pp. 243-245 ◽  
Author(s):  
Jordi Alsina ◽  
George Barany ◽  
Fernando Albericio ◽  
Steven A. Kates
Keyword(s):  
Carboxylic Acids ◽  
Phosphonium Salt ◽  
Side Reaction ◽  
Coupling Reagents

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

scholarly journals Total synthesis of the endogenous inflammation resolving lipid resolvin D2 using a common lynchpin

2013 ◽  
Vol 9 ◽  
pp. 2762-2766 ◽  
Author(s):  
John Li ◽  
May May Leong ◽  
Alastair Stewart ◽  
Mark A Rizzacasa
Keyword(s):  
Total Synthesis ◽  
Wittig Reaction ◽  
Phosphonium Salt ◽  
Ester Hydrolysis ◽  
Sonogashira Coupling ◽  
Partial Reduction ◽  
Vinyl Iodide ◽  
Key Steps

The total synthesis of the endogenous inflammation resolving eicosanoid resolvin D2 (1) is described. The key steps involved a Wittig reaction between aldehyde 5 and the ylide derived from phosphonium salt 6 to give enyne 17 and condensation of the same ylide with aldehyde 7 to afford enyne 11. Desilylation of 11 followed by hydrozirconation and iodination gave the vinyl iodide 4 and Sonogashira coupling between this compound and enyne 3 provided alkyne 18. Acetonide deprotection, partial reduction and ester hydrolysis then gave resolvin D2 (1).

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