Regioselective Solid-Phase Synthesis of Peptide Analogues Containing 3,4- or 3,5-Disubstituted Isoxazole as s-cis or s-trans Peptide Bond Mimics

2019 ◽  
Vol 2019 (20) ◽  
pp. 3134-3141 ◽  
Author(s):  
Pierrick Bruyat ◽  
Ludovic Jean ◽  
Pierre-Yves Renard
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Peptide Bond ◽  
Phase Synthesis ◽  
Peptide Analogues

Parallel Solid-Phase Synthesis of Partially Modified Retro and Retro-Inverso ψ[NHCH(CF3)]-Gly Peptides

2002 ◽  
Vol 67 (9) ◽  
pp. 1305-1319 ◽  
Author(s):  
Monica Sani ◽  
Pierfrancesco Bravo ◽  
Alessandro Volonterio ◽  
Matteo Zanda
Keyword(s):  
Amino Acid ◽  
Mild Condition ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Peptide Bond ◽  
Amino Acid Esters ◽  
Phase Synthesis ◽  
Acid Esters

The parallel solid-phase synthesis of small libraries of molecules belonging to a novel class of retro and retro-inverso peptides having a ψ[NHCH(CF3)] surrogate of the conventional retro-peptide bond (NH-CO) has been accomplished. Key step for the synthesis of the -NHCH(CF3)- unit is a Michael-type N-addition of resin bound α-amino acid esters H-AA1-OWang (1), dipeptide H-Val-Gly-OWang (8), and tripeptide H-Val-Val-Ala-OWang (12) to (S)-3-(E-enoyl)-1,3-oxazolidin-2-one (3), which took place very effectively under mild condition. Chemoselective exocyclic oxazolidinone cleavage, followed by parallel couplings of the resulting polymer-bound pseudopeptides WangO-AA1-ψ[NHCH(CF3)]-Gly-OH (5), WangO-Gly-Val-ψ[NHCH(CF3)]-Gly-OH (10), and WangO-Ala-Val-Val-ψ[NHCH(CF3)]-Gly-OH (14) with different α-amino acid esters afforded, after release from the resin, a representative set of ψ[NHCH(CF3)] retro and retro-inverso tripeptides HO-AA1-ψ[NHCH(CF3)]-Gly-AA2-OX1 (7), tetrapeptides HO-Gly-Val-ψ[NHCH(CF3)]-Gly-AA3-OX2 (11), and pentapeptides HO-Ala-Val-Val-ψ[NHCH(CF3)]-Gly-AA4-OX3 (15), respectively, with good to excellent purity in all cases.

scholarly journals The Problem of Aspartimide Formation During Protein Chemical Synthesis Using SEA-Mediated Ligation

2019 ◽  
Author(s):  
Jennifer Bouchenna ◽  
Magalie Sénéchal ◽  
Hervé Drobecq ◽  
Jérôme Vicogne ◽  
Oleg Melnyk
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Side Reaction ◽  
Peptide Bond ◽  
Protein Targets ◽  
Chemical Ligation ◽  
Phase Synthesis ◽  
Bond Forming ◽  
Aspartimide Formation ◽  
Peptide Segments

Aspartimide formation often complicates the solid phase synthesis of peptides. Much less discussed is the potential occurrence of this side-reaction during the coupling of peptide segments using chemoselective peptide bond forming reactions such as the native chemical ligation and extended methods. Here we describe how to manage this problem using bis(2-sulfenylethyl)amido (SEA)-mediated ligation and SUMO-2/SUMO-3 as protein targets.<br>

Convenient Solid-Phase Synthesis of Diethylenetriaminepenta-Acetic Acid (DTPA)– Conjugated Cyclic RGD Peptide Analogues

2005 ◽  
Vol 20 (5) ◽  
pp. 547-556 ◽  
Author(s):  
Wei Wang ◽  
John S. McMurray ◽  
Qingping Wu ◽  
Martin L. Campbell ◽  
Chun Li
Keyword(s):  
Acetic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Rgd Peptide ◽  
Phase Synthesis ◽  
Peptide Analogues

Solid-phase synthesis of nonhydrolyzable phosphotyrosyl peptide analogues with Nα-Fmoc-(O,O-di-t-butyl)phosphono-p-methylphenylalanine

1991 ◽  
Vol 32 (43) ◽  
pp. 6061-6064 ◽  
Author(s):  
Steven E. Shoelson ◽  
Swati Chatterjee ◽  
Manas Chaudhuri ◽  
Terrence R. Burke
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Peptide Analogues

Synthesis and application of N-Boc-L-2-amino-4-(diethylphosphono)-4,4-difluorobutanoic acid for solid-phase synthesis of nonhydrolyzable phosphoserine peptide analogues

1995 ◽  
Vol 36 (6) ◽  
pp. 927-930 ◽  
Author(s):  
Akira Otaka ◽  
Kengo Miyoshi ◽  
Terrence R Burke ◽  
Peter P Roller ◽  
Hideki Kubota ◽  
...  
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Peptide Analogues

scholarly journals Solid-Phase Synthesis of an Insect Pyrokinin Analog Incorporating an Imidazoline Ring as Isosteric Replacement of a trans Peptide Bond

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3271
Author(s):  
Krzysztof Kaczmarek ◽  
Barbara Pacholczyk-Sienicka ◽  
Łukasz Albrecht ◽  
Janusz Zabrocki ◽  
Ronald J. Nachman
Keyword(s):  
Bioactive Peptides ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Peptide Bond ◽  
Synthetic Method ◽  
Phase Synthesis ◽  
Iminium Salt ◽  
Diaminopropanoic Acid ◽  
Imidazoline Ring ◽  
Ring Motif

A facile solid-phase synthetic method for incorporating the imidazoline ring motif, a surrogate for a trans peptide bond, into bioactive peptides is reported. The example described is the synthesis of an imidazoline peptidomimetic analog of an insect pyrokinin neuropeptide via a cyclization reaction of an iminium salt generated from the preceding amino acid and 2,4-diaminopropanoic acid (Dap).

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