Further studies on the protection of histidine side chains in peptide synthesis: the use of the π-benzyloxymethyl group

1982 ◽  
pp. 1553-1561 ◽  
Author(s):  
Tom Brown ◽  
John H. Jones ◽  
John D. Richards
Keyword(s):  
Peptide Synthesis ◽  
Side Chains

A Strategy for Thioamide Incorporation During Fmoc Solid-Phase Peptide Synthesis with Robust Stereochemical Integrity

2019 ◽  
Author(s):  
luis camacho III ◽  
Bryan J. Lampkin ◽  
Brett VanVeller
Keyword(s):  
Amino Acid ◽  
Functional Groups ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Side Chains ◽  
Amino Acid Side Chains ◽  
Peptide Elongation

We describe a method to protect the sensitive stereochemistry of the thioamide—in analogy to the protection of the functional groups of amino acid side chains—in order to preserve the thioamide moiety during peptide elongation.<br>

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.

In-Peptide Synthesis of Imidazolidin-2-one Scaffolds, Equippable with Proteinogenic or Taggable/Linkable Side Chains, General Promoters of Unusual Secondary Structures

2019 ◽  
Vol 84 (9) ◽  
pp. 4992-5004 ◽  
Author(s):  
Rossella De Marco ◽  
Junwei Zhao ◽  
Arianna Greco ◽  
Simone Ioannone ◽  
Luca Gentilucci
Keyword(s):  
Peptide Synthesis ◽  
Secondary Structures ◽  
Side Chains

N-Methylamino Acids in Peptide Synthesis. II. A New Synthesis of N-Benzyloxycarbonyl, N-Methylamino Acids

1973 ◽  
Vol 51 (12) ◽  
pp. 1915-1919 ◽  
Author(s):  
John R. McDermott ◽  
N. Leo Benoiton
Keyword(s):  
Amino Acids ◽  
Methyl Iodide ◽  
Peptide Synthesis ◽  
Side Chains ◽  
Butyl Group ◽  
New Synthesis ◽  
Derivatives Of

Reaction of N-benzyloxycarbonyl derivatives of aliphatic amino acids, and threonine, aspartic, and glutamic acids whose side-chains were protected with the t-butyl group, gave the corresponding N-methylamino acid derivatives in good yields. The methionine derivative could be obtained by using only one mol of methyl iodide. Derivatives of threonine, and aspartic and glutamic acids whose side-chains were not protected could not be methylated. Analysis of the crude products of methylation in three cases showed that they contained 0–1% of racemized material.

Synthesis and chiroptical properties of heterodetic cyclic hexapeptides related to oxytocin ring moiety

1980 ◽  
Vol 45 (4) ◽  
pp. 1109-1131 ◽  
Author(s):  
Ivo Frič ◽  
Lyudmila I. Leonteva ◽  
Petr Maloň ◽  
Karel Jošt ◽  
Karel Bláha
Keyword(s):  
Amino Acid ◽  
Amino Acid Sequence ◽  
Peptide Synthesis ◽  
Spatial Arrangement ◽  
Cd Spectroscopy ◽  
Side Chains ◽  
Peptide Backbone ◽  
Chiroptical Properties ◽  
Disulfide Group ◽  
Cyclic Hexapeptides

Cyclic disulfides of cysteinyl-tetraglycyl-cysteine (Ia), cysteinyl-tyrosyl-triglycyl-cysteine (Ib) and cysteinyl-tyrosyl-isoleucyl-diglycyl-cysteine (Ic) were synthesized by classical methods of peptide synthesis. The actions of solvent and of side chains in the positions 2 and 3 on the conformational arrangement of the peptide backbone and the disulfide group were investigated by means of CD spectroscopy. Some mechanisms which co-operate in stabilizing the oxytocin conformation were identified. Hence, it may be deduced, that the amino acid sequence in the positions 1-3 determines the spatial arrangement characteristic for oxytocin, at least in a protonating medium.

A Strategy for Thioamide Incorporation During Fmoc Solid-Phase Peptide Synthesis with Robust Stereochemical Integrity

2019 ◽  
Author(s):  
luis camacho III ◽  
Bryan J. Lampkin ◽  
Brett VanVeller
Keyword(s):  
Amino Acid ◽  
Functional Groups ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Side Chains ◽  
Amino Acid Side Chains ◽  
Peptide Elongation

We describe a method to protect the sensitive stereochemistry of the thioamide—in analogy to the protection of the functional groups of amino acid side chains—in order to preserve the thioamide moiety during peptide elongation.<br>

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