ChemInform Abstract: “Head-to-Tail” Cyclization of Hexapeptides Using Different Coupling Reagents

ChemInform ◽  
2010 ◽  
Vol 24 (37) ◽  
pp. no-no
Author(s):  
S. ZIMMER ◽  
E. HOFFMANN ◽  
G. JUNG ◽  
H. KESSLER
Keyword(s):  
Coupling Reagents ◽  
Head To Tail Cyclization

scholarly journals Spontaneous head-to-tail cyclization of unprotected linear peptides with the KAHA ligation

2015 ◽  
Vol 6 (8) ◽  
pp. 4889-4896 ◽  
Author(s):  
Florian Rohrbacher ◽  
Gildas Deniau ◽  
Anatol Luther ◽  
Jeffrey W. Bode
Keyword(s):  
Cyclic Peptides ◽  
Mechanistic Study ◽  
Coupling Reagents ◽  
Head To Tail Cyclization

The α-ketoacid–hydroxylamine (KAHA) ligation enables the direct cyclization of unprotected peptides upon cleavage, without coupling reagents or purification of precursors. We report the synthesis of a library of 24 cyclic peptides and a detailed mechanistic study.

“Head-to-Tail” Cyclization of Hexapeptides Using Different Coupling Reagents

1993 ◽  
Vol 1993 (5) ◽  
pp. 497-501 ◽  
Author(s):  
Susanne Zimmer ◽  
Eike Hoffmann ◽  
Günther Jung ◽  
Horst Kessler
Keyword(s):  
Coupling Reagents ◽  
Head To Tail Cyclization

scholarly journals Silicon compounds as stoichiometric coupling reagents for direct amidation

2021 ◽  
Author(s):  
Joshua J. Davies ◽  
D. Christopher Braddock ◽  
Paul D. Lickiss
Keyword(s):  
Carboxylic Acids ◽  
Coupling Reagents ◽  
Silicon Compounds ◽  
Direct Amidation

This review covers all the reported use of stoichiometric silicon reagents for direct amidation of carboxylic acids with amines, commencing with the first example in 1969 up until April 2021. 

scholarly journals Racemization-free synthesis of Nα-2-thiophenoyl-phenylalanine-2-morpholinoanilide enantiomers and their antimycobacterial activity

Amino Acids ◽  
2021 ◽  
Author(s):  
Lea Mann ◽  
Markus Lang ◽  
Philipp Schulze ◽  
Jan Henrik Halz ◽  
René Csuk ◽  
...  
Keyword(s):  
Title Compound ◽  
Mammalian Cells ◽  
Antimycobacterial Activity ◽  
Lead Compound ◽  
Coupling Reagents ◽  
Hydrogen Bonding Interactions ◽  
Amide Coupling ◽  
Subsequent Separation ◽  
Synthetic Routes ◽  
Insight Into

AbstractNα-2-thiophenoyl-d-phenylalanine-2-morpholinoanilide (MMV688845, IUPAC: N-(1-((2-morpholinophenyl)amino)-1-oxo-3-phenylpropan-2-yl)thiophene-2-carboxamide) from the Pathogen Box® library (Medicines for Malaria Ventures, MMV) is a promising lead compound for antimycobacterial drug development. Two straightforward synthetic routes to the title compound starting from phenylalanine or its Boc-protected derivative are reported. Employing Boc-phenylalanine as starting material and the T3P® and PyBOP® amide coupling reagents enables racemization-free synthesis, avoiding the need for subsequent separation of the enantiomers. The crystal structure of the racemic counterpart gives insight into the molecular structure and hydrogen bonding interactions in the solid state. The R-enantiomer of the title compound (derived from d-phenylalanine) exhibits activity against non-pathogenic and pathogenic mycobacterial strains, whereas the S-enantiomer is inactive. Neither of the enantiomers and the racemate of the title compound shows cytotoxicity against various mammalian cells.

scholarly journals Site-specific Umpolung amidation of carboxylic acids via triplet synergistic catalysis

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Yunyun Ning ◽  
Shuaishuai Wang ◽  
Muzi Li ◽  
Jie Han ◽  
Chengjian Zhu ◽  
...  
Keyword(s):  
Carboxylic Acids ◽  
Functional Group ◽  
Amide Bond ◽  
Coupling Reagents ◽  
Complex Molecules ◽  
Bond Forming ◽  
Synergistic Catalysis ◽  
Wide Range ◽  
Amidation Reaction ◽  
Forming Methods

AbstractDevelopment of catalytic amide bond-forming methods is important because they could potentially address the existing limitations of classical methods using superstoichiometric activating reagents. In this paper, we disclose an Umpolung amidation reaction of carboxylic acids with nitroarenes and nitroalkanes enabled by the triplet synergistic catalysis of FeI2, P(V)/P(III) and photoredox catalysis, which avoids the production of byproducts from stoichiometric coupling reagents. A wide range of carboxylic acids, including aliphatic, aromatic and alkenyl acids participate smoothly in such reactions, generating structurally diverse amides in good yields (86 examples, up to 97% yield). This Umpolung amidation strategy opens a method to address challenging regioselectivity issues between nucleophilic functional groups, and complements the functional group compatibility of the classical amidation protocols. The synthetic robustness of the reaction is demonstrated by late-stage modification of complex molecules and gram-scale applications.

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: Tetraphenylporphyrins as Coupling Reagents and Corrosion Inhibitors.

ChemInform ◽  
2010 ◽  
Vol 24 (17) ◽  
pp. no-no
Author(s):  
B. MEYER-ROSCHER ◽  
T. SIEMENS ◽  
H. BROCKMANN
Keyword(s):  
Corrosion Inhibitors ◽  
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
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