Extended Solution-phase Peptide Synthesis Strategy Using Isostearyl-Mixed Anhydride Coupling and a New C-Terminal Silyl Ester-Protecting Group for N-Methylated Cyclic Peptide Production

2021 ◽  
Vol 25 (9) ◽  
pp. 2029-2038
Author(s):  
Akihiro Nagaya ◽  
Shota Murase ◽  
Yuji Mimori ◽  
Kazuya Wakui ◽  
Madoka Yoshino ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Cyclic Peptide ◽  
Solution Phase ◽  
Protecting Group ◽  
Mixed Anhydride ◽  
Silyl Ester ◽  
Synthesis Strategy

scholarly journals Solution-Phase Fmoc-Based Peptide Synthesis for DNA-Encoded Chemical Libraries: Reaction Conditions, Protecting Group Strategies, and Pitfalls

2020 ◽  
Vol 22 (12) ◽  
pp. 833-843
Author(s):  
Olivier B. C. Monty ◽  
Nicholas Simmons ◽  
Srinivas Chamakuri ◽  
Martin M. Matzuk ◽  
Damian W. Young
Keyword(s):  
Peptide Synthesis ◽  
Solution Phase ◽  
Protecting Group ◽  
Reaction Conditions ◽  
Chemical Libraries

Synthesis of the Simple Peptide Model Ac-Abu(PO3H2)-NHMe

1992 ◽  
Vol 45 (4) ◽  
pp. 777 ◽  
Author(s):  
RM Valerio ◽  
JW Perich ◽  
PF Alewood ◽  
G Tong ◽  
RB Johns
Keyword(s):  
Acetic Acid ◽  
Simple Model ◽  
Acid Derivative ◽  
Peptide Synthesis ◽  
Solution Phase ◽  
Quantitative Yield ◽  
Initial Reaction ◽  
Mixed Anhydride ◽  
Butanoic Acid ◽  
Acid Cleavage

The simple model substrate AC-L-Abu(PO3H2)- NHMe was prepared by the use of the protected 4( diethylphosphono ) butanoic acid derivative Boc -Abu(PO3Et2)-OH in the Boc mode of solution phase peptide synthesis. The protected peptide model Ac-Abu(P03Et2)- NHMe was prepared by initial reaction of the isobutoxycarbonyl mixed anhydride of Boc-Abu(PO3Et2)-OH with N-methylamine followed by cleavage of the Boc group from Boc -Abu(PO3Et2)- NHMe with 4 M HCl/dioxan and N- acetylation of H-Abu(PO3Et2)-NHMe.HCl with the isobutoxycarbonyl mixed anhydride of acetic acid. Cleavage of the phosphonate ethyl groups was effected with 33% hydrogen bromidelacetic acid or 10% bromotrimethylsilane/acetonitrile to give AC-L-Abu(PO3H2)-NHMe in near-quantitative yield.

scholarly journals Folding and fluorescence enhancement with strong odd–even effect for a series of merocyanine dye oligomers

2021 ◽  
Author(s):  
Xiaobo Hu ◽  
Alexander Schulz ◽  
Joachim O. Lindner ◽  
Matthias Grüne ◽  
David Bialas ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Fluorescence Enhancement ◽  
Synthesis Strategy

A series of merocyanine (MC) oligomers with a varying number of chromophores from two to six has been synthesized via a peptide synthesis strategy.

o-Nitrobenzoyl group as a new amino protecting group for peptide synthesis and the synthesis of some anthranilyl peptides

Tetrahedron ◽  
1973 ◽  
Vol 29 (4) ◽  
pp. 625-628 ◽  
Author(s):  
A.K. Koul ◽  
J.M. Bachhawat ◽  
B. Prashad ◽  
N.S. Ramegowda ◽  
A.K. Mathur ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Protecting Group

The 2-chloro-3-indenylmethyloxycarbonyl and benz[f]inden-3-ylmethyloxycarbonyl base-sensitive amino-protecting group. Application to an inverse Merrifield approach to peptide synthesis

1990 ◽  
Vol 55 (1) ◽  
pp. 251-259 ◽  
Author(s):  
Louis A. Carpino ◽  
Beri J. Cohen ◽  
Yao Zhong Lin ◽  
Kenton E. Stephens ◽  
Salvatore A. Triolo
Keyword(s):  
Peptide Synthesis ◽  
Protecting Group

Multi-pin peptide synthesis strategy for T cell determinant analysis

1990 ◽  
Vol 134 (1) ◽  
pp. 23-33 ◽  
Author(s):  
N. Joe Maeji ◽  
Andrew M. Bray ◽  
H. Mario Geysen
Keyword(s):  
T Cell ◽  
Peptide Synthesis ◽  
Synthesis Strategy ◽  
Determinant Analysis

scholarly journals Application of an Automated Synthesis Suite to Parallel Solution-Phase Peptide Synthesis.

2001 ◽  
Vol 49 (9) ◽  
pp. 1147-1154 ◽  
Author(s):  
Noritaka KURODA ◽  
Taeko HATTORI ◽  
Yoko FUJIOKA ◽  
David G. CORK ◽  
Chieko KITADA ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Solution Phase ◽  
Automated Synthesis ◽  
Parallel Solution

ChemInform Abstract: New Strategies for an Efficient Removal of the 9-Fluorenylmethoxycarbonyl (Fmoc) Protecting Group in the Peptide Synthesis.

ChemInform ◽  
2010 ◽  
Vol 31 (16) ◽  
pp. no-no
Author(s):  
Antonella Leggio ◽  
Angelo Liguori ◽  
Anna Napoli ◽  
Carlo Siciliano ◽  
Giovanni Sindona
Keyword(s):  
Peptide Synthesis ◽  
Protecting Group ◽  
Efficient Removal ◽  
Fmoc Protecting Group ◽  
New Strategies

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.

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