Pseudoproline Dipeptides in Fmoc SolidPhase Peptide Synthesis

Neuland has expertise in both solution phase and solid phase synthesis methodologies. We have delivered 32 kg of a decapeptide for a US based company by solution phase segment condensation of two pentapeptide key starting materials. The N-terminal KSM utilized a pseudoproline at its C-terminus. (Further details of this project can be found in ‘Projects Realised’.)

Pseudoproline dipeptides have many uses in peptide synthesis

Most peptides between five and sixty amino acids are produced by standard solid phase peptide synthesis (SPPS) procedures. Multiple kilos of shorter length (up to 10 amino acids) are produced by solution phase methods. For longer peptides, containing up to 120 amino acids, segment condensation and ligation techniques are employed.

Custom Peptide Synthesis; Custom Peptide ..

For the synthesis of long peptides we recommend to use a protocol in which systematic double coupling is followed by capping.

Synthetic Peptides are finding increasing use as therapeutics, diagnostics, for antibody production, and as tools for understanding biological processes. Neuland’s peptide synthesis services include production of peptides from milligrams to multi-kilogram scale by standard sequential chemical peptide syntheses and segment condensation strategies.

ChemPep: One stop for peptide synthesis

Hence, pseudoprolines fulfill two functions simultaneously: theyserve (1) as temporary side-chain protection for Ser, Thr, and Cysand (2) as solubilizing building blocks to increase solvation andcoupling rates during synthesis and in subsequent chainassembly. Pseudoprolines are obtained by reacting the free aminoacids with aldehydes or ketone. Thecoupling of amino acid derivatives to a growing peptide chaincontaining pseudoproline generally resultsin low yields because of the sterically hindered nature of theoxazolidine (thiazolidine) ring system and the decreasednucleophilicity of the nitrogen atom. Consequently, thepreformation of suitably protected dipeptide derivatives of thetype -Xaa1-Oxa/THz-OH is preferable for usein peptide synthesis. Two conceptually different approaches arefeasible for preparing oxazolidine- andthiazolidine-ring-containing dipeptide derivatives: (1) the acylation of Ser- orThr-derived oxazolidines or Cys-derived thiazolidines using acidfluorides or N-carboxyanhydrides (NCA); and (2) the directinsertion of the oxazolidine systems into dipeptides(post-insertion) containing C-terminal Ser or Thr. The method ofchoice strongly depends on the nature of the pseudoproline as welIas on the substituents at C2 of the cyclic system.

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With extensive experience in solid and solution phase synthesis, ChemPep provides premium quality custom peptides with the most competitive price.

Up to 100 amino acids; Peptides with different quantities: from mg to kg...

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In peptide synthesis diketopiperazine formation is a notorious side-reaction at the dipeptide stage and is particularly prone to occur in Fmoc based SPPS because of its mechanism.