ChemInform Abstract: EFFECT OF TRIFLUOROACETIC ACID UPON BOC-AMINOACYL- AND BOC-PEPTIDYL-RESINS. DESCRIPTION OF A NEW POLYMERIC SUPPORT FOR SOLID PHASE PEPTIDE SYNTHESIS

1979 ◽  
Vol 10 (52) ◽  
Author(s):  
E. GIRALT ◽  
D. ANDREU ◽  
L. RAFECAS
Keyword(s):  
Peptide Synthesis ◽  
Trifluoroacetic Acid ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Polymeric Support

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.

Dramatically enhanced N→O acyl migration during the trifluoroacetic acid-based deprotection step in solid phase peptide synthesis

2005 ◽  
Vol 46 (8) ◽  
pp. 1361-1364 ◽  
Author(s):  
Louis A. Carpino ◽  
Eberhard Krause ◽  
Calin Dan Sferdean ◽  
Michael Bienert ◽  
Michael Beyermann
Keyword(s):  
Peptide Synthesis ◽  
Trifluoroacetic Acid ◽  
Solid Phase ◽  
Acyl Migration ◽  
Solid Phase Peptide Synthesis

scholarly journals Evaluation of the Trifluoromethanosulfonic Acid/Trifluoroacetic Acid/Thioanisole Cleavage Procedure for Application in Solid-Phase Peptide Synthesis.

2001 ◽  
Vol 49 (9) ◽  
pp. 1089-1092 ◽  
Author(s):  
Guita N. JUBILUT ◽  
Eduardo M. CILLI ◽  
Mineko TOMINAGA ◽  
Antonio MIRANDA ◽  
Yoshio OKADA ◽  
...  
Keyword(s):  
Peptide Synthesis ◽  
Trifluoroacetic Acid ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis

scholarly journals Solid Phase Peptide Synthesis by Four Component Condensation: Peptide Formation on an Isocyano Polymer Support

1981 ◽  
Vol 36 (9) ◽  
pp. 1202-1203 ◽  
Author(s):  
Reza Arshady ◽  
Ivar Ugi
Keyword(s):  
Amino Acids ◽  
Peptide Synthesis ◽  
Trifluoroacetic Acid ◽  
Room Temperature ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Polymer Support ◽  
Small Peptides ◽  
Peptide Formation

Abstract Coupling of various protected amino acids or small peptides on an isocyano polymer and in the presence of 1 -methyl-3-formylindole demonstrates the feasibility of peptide formation by four component condensation on a polymer support, and the final peptide is detached from the resin by 50% trifluoroacetic acid in aceto-nitrile at room temperature.

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