Development of a solid-phase traceless-Ugi multicomponent reaction for backbone anchoring and cyclic peptide synthesis

2018 ◽  
Vol 111 (1) ◽  
pp. e24044 ◽  
Author(s):  
Steve Jobin ◽  
Catherine Beaumont ◽  
Eric Biron
Keyword(s):  
Peptide Synthesis ◽  
Multicomponent Reaction ◽  
Cyclic Peptide ◽  
Solid Phase ◽  
Cyclic Peptide Synthesis

scholarly journals Recyclable hypervalent-iodine-mediated solid-phase peptide synthesis and cyclic peptide synthesis

2018 ◽  
Vol 14 ◽  
pp. 1112-1119 ◽  
Author(s):  
Dan Liu ◽  
Ya-Li Guo ◽  
Jin Qu ◽  
Chi Zhang
Keyword(s):  
Peptide Synthesis ◽  
Cyclic Peptide ◽  
Solid Phase ◽  
Biological Activities ◽  
Solid Phase Peptide Synthesis ◽  
Coupling Reaction ◽  
Hypervalent Iodine ◽  
Peptide Coupling ◽  
Cyclic Peptide Synthesis ◽  
Cyclic Heptapeptide

The system of the hypervalent iodine(III) reagent FPID and (4-MeOC6H4)3P was successfully applied to solid-phase peptide synthesis and cyclic peptide synthesis. Four peptides with biological activities were synthesized through SPPS and the bioactive cyclic heptapeptide pseudostellarin D was obtained via solution-phase peptide synthesis. It is worth noting that FPID can be readily regenerated after the peptide coupling reaction.

scholarly journals Pyrrole-Mediated Peptide Cyclization Identified through Genetically Reprogrammed Peptide Synthesis

Biomedicines ◽  
2018 ◽  
Vol 6 (4) ◽  
pp. 99 ◽  
Author(s):  
Klaas Decoene ◽  
Willem Vannecke ◽  
Toby Passioura ◽  
Hiroaki Suga ◽  
Annemieke Madder
Keyword(s):  
Peptide Synthesis ◽  
Cyclic Peptide ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Screening Method ◽  
In Vitro Translation ◽  
Side Chain ◽  
One Pot ◽  
Depth Analysis

Flexible in vitro translation (FIT) was used as a screening method to uncover a new methodology for peptide constraining based on the attack of a nucleophilic side-chain functionality onto an oxidized furylalanine side chain. A set of template peptides, each containing furylalanine as furan-modified amino acid and a nucleophilic residue (Cys, His, Lys, Arg, Ser, or Tyr), was produced through FIT. The translation mixtures were treated with N-bromosuccinimide (NBS) to achieve selective furan oxidation and subsequent MALDI analysis demonstrated Lys and Ser as promising residues for cyclisation. Solid-phase peptide synthesis (SPPS) was used to synthesize suitable amounts of material for further in-depth analysis and characterisation. It was found that in the case of the peptide containing lysine next to a furylalanine residue, a one-pot oxidation and reduction reaction leads to the generation of a cyclic peptide featuring a pyrrole moiety as cyclisation motif, resulting from the attack of the lysine side chain onto the oxidized furylalanine side chain. Structural evidence was provided via NMR and the generality of the methodology was explored. We hereby expand the scope of our previously developed furan-based peptide labeling and crosslinking strategy.

Cyclic Peptide Synthesis with Thioacids

2010 ◽  
Vol 12 (14) ◽  
pp. 3254-3257 ◽  
Author(s):  
Kaname Sasaki ◽  
David Crich
Keyword(s):  
Peptide Synthesis ◽  
Cyclic Peptide ◽  
Cyclic Peptide Synthesis

scholarly journals Novel Cyclic Lipopeptide Antibiotics: Effects of Acyl Chain Length and Position

2020 ◽  
Vol 21 (16) ◽  
pp. 5829 ◽  
Author(s):  
Signe Kaustrup Jensen ◽  
Thomas T. Thomsen ◽  
Alberto Oddo ◽  
Henrik Franzyk ◽  
Anders Løbner-Olesen ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Fatty Acid ◽  
Chain Length ◽  
Peptide Synthesis ◽  
Hemolytic Activity ◽  
Cyclic Peptide ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Resistant Bacteria ◽  
Cyclic Lipopeptide

Multidrug-resistant bacteria are a global health problem. One of the last-resort antibiotics against Gram-negative bacteria is the cyclic lipopeptide colistin, displaying a flexible linker with a fatty acid moiety. The aim of the present project was to investigate the effect on antimicrobial activity of introducing fatty acid moieties of different lengths and in different positions in a cyclic peptide, S3(B), containing a flexible linker. The lipidated analogues of S3(B) were synthesized by 9-fluorenylmethoxycarbonyl (Fmoc) solid-phase peptide synthesis. Following assembly of the linear peptide by Fmoc solid-phase peptide synthesis, on-resin head-to-tail cyclization and fatty acid acylation were performed. The antimicrobial activity was determined against the ESKAPE pathogens, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, and Escherichia coli. Furthermore, hemolytic activity was determined against human erythrocytes. A total of 18 cyclic lipopeptides were synthesized and characterized. It was found that introduction of fatty acids in positions next to the flexible linker was more strongly linked to antimicrobial activity. The fatty acid length altered the overall hydrophobicity, which was the driving force for both high antimicrobial and hemolytic activity. Peptides became highly hemolytic when carbon-chain length exceeded 10 (i.e., C10), overlapping with the optimum for antimicrobial activity (i.e., C8–C12). The most promising candidate (C8)5 showed antimicrobial activity corresponding to that of S3(B), but with an improved hemolytic profile. Finally, (C8)5 was further investigated in a time-kill experiment.

Disulfide-Driven Cyclic Peptide Synthesis of Human Endothelin-2 with a Solid-Supported Npys-Cl

2019 ◽  
Vol 85 (3) ◽  
pp. 1495-1503 ◽  
Author(s):  
Akihiro Taguchi ◽  
Kiyotaka Kobayashi ◽  
Yan Cui ◽  
Kentaro Takayama ◽  
Atsuhiko Taniguchi ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Cyclic Peptide ◽  
Cyclic Peptide Synthesis

Facile Synthesis of Peptidyl Salicylaldehyde Esters and Its Use in Cyclic Peptide Synthesis

2013 ◽  
Vol 15 (20) ◽  
pp. 5182-5185 ◽  
Author(s):  
Jun-Feng Zhao ◽  
Xiao-Hong Zhang ◽  
Ying-Jie Ding ◽  
Yong-Sheng Yang ◽  
Xiao-Bao Bi ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Cyclic Peptide ◽  
Facile Synthesis ◽  
Cyclic Peptide Synthesis
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