ChemInform Abstract: A New Method for the Solid Phase Synthesis of Hydroxyethylamine Peptide Bond Isosters: Synthesis of an HIV-1 Protease Inhibitor and of a β-Casomorphin-5 Analogue.

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.

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Solid Phase Synthesis of Novel Pyrrolidinedione Analogs as Potent HIV-1 Integrase Inhibitors

Journal of Combinatorial Chemistry ◽

10.1021/cc9001026 ◽

2010 ◽

Vol 12 (1) ◽

pp. 84-90 ◽

Cited By ~ 16

Author(s):

Annapurna Pendri ◽

Timothy L. Troyer ◽

Michael J. Sofia ◽

Michael A. Walker ◽

B. Narasimhulu Naidu ◽

...

Keyword(s):

Solid Phase Synthesis ◽

Solid Phase ◽

Integrase Inhibitors ◽

Phase Synthesis ◽

Hiv 1

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Solid-phase synthesis and thermal denaturation study of cyclic PNAs targeting the HIV-1 TAR RNA loop

Bioorganic & Medicinal Chemistry Letters ◽

10.1016/j.bmcl.2007.07.030 ◽

2007 ◽

Vol 17 (21) ◽

pp. 6026-6030 ◽

Cited By ~ 3

Author(s):

Gregory Upert ◽

Mohamed Mehiri ◽

Audrey Di Giorgio ◽

Roger Condom ◽

Nadia Patino

Keyword(s):

Thermal Denaturation ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Phase Synthesis ◽

Thermal Denaturation Study ◽

Tar Rna ◽

Hiv 1

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Solid-Phase Synthesis of the Alkenyldiarylmethane (ADAM) Series of Non-Nucleoside HIV-1 Reverse Transcriptase Inhibitors

The Journal of Organic Chemistry ◽

10.1021/jo0100291 ◽

2001 ◽

Vol 66 (18) ◽

pp. 5958-5964 ◽

Cited By ~ 15

Author(s):

Guozhang Xu ◽

Tracy L. Loftus ◽

Heather Wargo ◽

Jim A. Turpin ◽

Robert W. Buckheit, ◽

...

Keyword(s):

Reverse Transcriptase ◽

Solid Phase Synthesis ◽

Solid Phase ◽

Reverse Transcriptase Inhibitors ◽

Phase Synthesis ◽

Hiv 1

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

10.26434/chemrxiv.11409417 ◽

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>

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