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The solid phase now bears a dipeptide. This cycle is repeated to form the desired peptide chain. After all reactions are complete, the synthesised peptide is cleaved from the bead. The protecting groups for the amino groups mostly used in the peptide synthesis are 9-fluorenylmethyloxycarbonyl group and t-butyloxycarbonyl . A number of amino ...
These studies led to the need for peptide synthesis and, eventually, to the idea for solid phase peptide synthesis (SPPS) in 1959. In 1963, he was sole author of a classic paper in the Journal of the American Chemical Society in which he reported a method he called "solid phase peptide synthesis". [4]
The established method for the production of synthetic peptides in the lab is known as solid phase peptide synthesis (SPPS). [2] Pioneered by Robert Bruce Merrifield, [4] [5] SPPS allows the rapid assembly of a peptide chain through successive reactions of amino acid derivatives on a macroscopically insoluble solvent-swollen beaded resin support.
Combinatorial split-mix (split and pool) synthesis [12] [13] is based on the solid-phase synthesis developed by Merrifield. [14] If a combinatorial peptide library is synthesized using 20 amino acids (or other kinds of building blocks) the bead form solid support is divided into 20 equal portions. This is followed by coupling a different amino ...
Due to the preference for a cis-amide bond [10] with the preceding residue of C2-substituted pseudoprolines, their incorporation results in a kink conformation of the peptide backbone, thus preventing peptide aggregation, self-association, or β-structure formation. Strategies for the use of Pseudoproline in Solid-Phase Peptide Synthesis (SPPS).
Within solid phase peptide synthesis (SPPS) there exist two strategies for the synthesis of glycopeptides, linear and convergent assembly. Linear assembly relies on the synthesis of building blocks and then the use of SPPS to attach the building block together. An outline of this approach is illustrated below. Scheme 1.
In general, peptides shorter than 8 amino acids are prepared more economically by solution chemistry. Peptides larger than 8 residues are generally assembled by solid phase chemistry. Solid phase peptide synthesis (SPPS) can be carried out either manually or in a fully automated fashion. Manual synthesis for short peptides is advantageous as it ...
Fmoc chemistry solid phase peptide synthesis techniques for generating peptide-thioesters are based on the synthesis of peptide hydrazides that are converted to peptide thioesters post-synthetically. Polypeptide C-terminal thioesters can also be produced in situ, using so-called N,S-acyl shift systems.