scholarly journals Diversity-oriented synthesis of peptide-boronic acids by a versatile building-block approach

2020 ◽  
Vol 11 (36) ◽  
pp. 9898-9903 ◽  
Author(s):  
Stefan P. A. Hinkes ◽  
Severin Kämmerer ◽  
Christian D. P. Klein
Keyword(s):  
Peptide Synthesis ◽  
Building Block ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Boronic Acids ◽  
Diversity Oriented Synthesis ◽  
Block Approach

Decarboxylative borylation and monophasic transesterification yields Fmoc-α-aminoboronates for solid-phase peptide synthesis.

scholarly journals Efficient and Reproducible Synthesis of an Fmoc-protected Tn Antigen

2021 ◽  
Author(s):  
Michael R. Reynolds ◽  
Sabrina Piazza ◽  
Jonathan Chiaramonte ◽  
Fabiola A. Chapa-Villarreal ◽  
John Trant
Keyword(s):  
Total Synthesis ◽  
Peptide Synthesis ◽  
Building Block ◽  
Large Scale ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Tn Antigen ◽  
Palladium Catalyzed ◽  
Glycosyl Donor ◽  
Antigen A

The total synthesis of the Thomsen-nouveau (Tn) antigen, a tumour-associated O-linked mucin glycopeptide, was achieved through a concise route. The key glycosylation step proved challenging to reproduce from the literature precedents and was most reliably accomplished using a palladium-catalyzed coupling between the glycosyl donor and Fmoc-functionalized serine acceptor to form the target in moderate yields. This is, to the best of our knowledge, the shortest synthesis reported from galactose for preparing this essential building block for large-scale solid phase peptide synthesis.

scholarly journals The synthesis of an EDTA-like chelating peptidomimetic building block suitable for solid-phase peptide synthesis

2017 ◽  
Vol 53 (17) ◽  
pp. 2634-2636 ◽  
Author(s):  
Jan Spengler ◽  
Michael Barker ◽  
Constanze Schelhorn ◽  
Jesús García ◽  
Maria J. Macias ◽  
...  
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Building Block ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis

A novo trifunctional EDTA-like peptidomimetic amino acid is described.

A silyl ether-protected building block for O-GlcNAcylated peptide synthesis to enable one-pot acidic deprotection

2021 ◽  
Vol 19 (37) ◽  
pp. 8014-8017
Author(s):  
Bingjia Yan ◽  
Wenyi Li ◽  
Christian P. R. Hackenberger
Keyword(s):  
Peptide Synthesis ◽  
Building Block ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Silyl Ether ◽  
One Pot

In this report, we introduce a novel building block for Fmoc/tBu solid phase peptide synthesis (SPPS) of β-linked O-GlcNAcylated peptides.

The Preparation of Solid-Supported Peptide Boronic Acids Derived from 4-Borono-L-phenylalanine and their Affinity for Alizarin

2007 ◽  
Vol 60 (11) ◽  
pp. 829 ◽  
Author(s):  
Peter J. Duggan ◽  
Daniel A. Offermann
Keyword(s):  
Peptide Synthesis ◽  
Boronic Acid ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Boronic Acids ◽  
Association Constants ◽  
Synthesis Methods ◽  
Selective Binding ◽  
Binding Characteristics ◽  
Potential Use

A library of solid-supported pentapeptide diboronic acids, a ‘lysine series’ and an ‘arginine series’, has been efficiently prepared using N-Fmoc-4-pinacolatoborono-l-phenylalanine and standard solid phase peptide synthesis methods. A technique for measuring the affinity of the chromophoric diol, alizarin, to the solid-supported peptide boronic acids has been developed. Considerable variation in alizarin binding strengths, both within and between arginine and lysine series was observed, with association constants in the range 200–1100 M–1 being recorded. The selective binding characteristics of these boronic acid–peptide hybrids suggest their potential use in carbohydrate sensors and cell-specific diagnostics and therapeutics.

Synthesis of Asparagusic Acid Modified Lysine and its Application in Solid-Phase Synthesis of Peptides with Enhanced Cellular Uptake

Synlett ◽  
2017 ◽  
Vol 29 (10) ◽  
pp. 1289-1292 ◽  
Author(s):  
Pablo Rivera-Fuentes ◽  
Alina Tirla ◽  
Moritz Hansen
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Cellular Uptake ◽  
Building Block ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Live Cells ◽  
Phase Synthesis ◽  
Scalable Synthesis

Cyclic disulfides, such as asparagusic acid, enhance the uptake of a variety of cargoes into live cells. Here, we report a robust and scalable synthesis of an asparagusic acid modified lysine. This amino acid can be used in solid-phase peptide synthesis. We confirmed that incorporation of this building block into the sequence of a peptide increases its cellular uptake substantially.

scholarly journals Synthetic peptides caged on histidine residues with a bisbipyridyl ruthenium(ii) complex that can be photolyzed by visible light

2015 ◽  
Vol 51 (25) ◽  
pp. 5501-5504 ◽  
Author(s):  
Jesús Mosquera ◽  
Mateo I. Sánchez ◽  
José L. Mascareñas ◽  
M. Eugenio Vázquez
Keyword(s):  
Visible Light ◽  
Peptide Synthesis ◽  
Building Block ◽  
Synthetic Peptides ◽  
Solid Phase ◽  
Ruthenium Complex ◽  
Solid Phase Peptide Synthesis ◽  
Side Chain ◽  
Histidine Residues

We report a light-sensitive histidine building block for Fmoc/tBu solid-phase peptide synthesis in which the imidazole side chain is coordinated to a ruthenium complex.

scholarly journals Efficient and Reproducible Synthesis of an Fmoc-protected Tn Antigen

2021 ◽  
Author(s):  
Michael R. Reynolds ◽  
Sabrina Piazza ◽  
Jonathan Chiaramonte ◽  
Fabiola A. Chapa-Villarreal ◽  
John Trant
Keyword(s):  
Total Synthesis ◽  
Peptide Synthesis ◽  
Building Block ◽  
Large Scale ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Tn Antigen ◽  
Palladium Catalyzed ◽  
Glycosyl Donor ◽  
Antigen A

The total synthesis of the Thomsen-nouveau (Tn) antigen, a tumour-associated O-linked mucin glycopeptide, was achieved through a concise route. The key glycosylation step proved challenging to reproduce from the literature precedents and was most reliably accomplished using a palladium-catalyzed coupling between the glycosyl donor and Fmoc-functionalized serine acceptor to form the target in moderate yields. This is, to the best of our knowledge, the shortest synthesis reported from galactose for preparing this essential building block for large-scale solid phase peptide synthesis.

scholarly journals Synthesis of an Fmoc-threonine bearing core-2 glycan: A building block for PSGL-1 via Fmoc-assisted solid-phase peptide synthesis

2010 ◽  
Vol 345 (11) ◽  
pp. 1541-1547 ◽  
Author(s):  
Venkata R. Krishnamurthy ◽  
Ann Dougherty ◽  
Medha Kamat ◽  
Xuezheng Song ◽  
Richard D. Cummings ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Building Block ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis

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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