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.

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.

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>

Instrumentation for automated solid phase peptide synthesis

1999 ◽  
Author(s):  
Linda E. Cammish ◽  
Steven A. Kates
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Reaction Vessel ◽  
Automated System ◽  
Polymeric Support ◽  
Simple Filtration ◽  
Subsequent Activation ◽  
Selection Of

The concept of solid phase peptide synthesis introduced by Merrifield in 1963 involves elongating a peptide chain on a polymeric support via a two-step repetitive process: removal of the Nα-protecting group and coupling of the next incoming amino acid. A second feature of the solid phase technique is that reagents are added in large excesses which can be removed by simple filtration and washing. Since these operations occur in a single reaction vessel, the entire process is amenable to automation. Essential requirements for a fully automatic synthesizer include a set of solvent and reagent reservoirs, as well as a suitable reaction vessel to contain the solid support and enable mixing with solvents and reagents. Additionally, a system is required for selection of specific solvents and reagents with accurate measurement for delivery to and removal from the reaction vessel, and a programmer to facilitate these automatic operations is necessary. The current commercially available instruments offer a variety of features in terms of their scale (15 mg to 5 kg of resin), chemical compatibility with 9-fluorenylmethyloxycarbonyl/tert-butyl (Fmoc/tBu) and tert-butyloxycarbonyl/ benzyl (Boc/Bzl)-based methods, software (reaction monitoring and feedback control), and flexibility (additional washing and multiple activation strategies). In addition, certain instruments are better suited for the synthesis of more complex peptides such as cyclic, phosphorylated, and glycosylated sequences while others possess the ability to assemble a large number of peptide sequences. The selection of an instrument is dependent on the requirements and demands of an individual laboratory. This chapter will describe the features of the currently available systems. As the field of solid phase synthesis evolved, manufacturers designed systems based on the synergy between chemistry and engineering. A key component to an instrument is the handling of amino acids and their subsequent activation to couple to a polymeric support. The goal of an automated system is to duplicate conditions that provide stability to reactive species that might decompose. Standard protocols for automated synthesis incorporate carbodiimide, phosphonium, and aminium/uronium reagents, preformed active esters, and acid fluorides. For further details on coupling methods, see Chapter 3. A second issue related to coupling chemistry is the time required to dissolve an amino acid and store this solution.

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.

Amino acid bromides: their utilization for difficult couplings in solid-phase peptide synthesis

2005 ◽  
Vol 46 (37) ◽  
pp. 6369-6371 ◽  
Author(s):  
Minghong Ni ◽  
Emiliano Esposito ◽  
Bernard Kaptein ◽  
Quirinus B. Broxterman ◽  
Alma Dal Pozzo
Keyword(s):  
Amino Acid ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis
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