New: Cysteine-Pseudoproline

Published on 03.03.2015

Pseudoprolines derived from Serine and Threonine have developed to standard building blocks for peptide synthesis since their invention. Now this technology is also available with Cysteine residues, as the corresponding 2,4-dimethoxyphenyl-pseudothiaproline is compatible with standard Fmoc/tBu protocols.

Pseudoprolines derived from Serine and Threonine have developed to standard building blocks for peptide synthesis since their invention by Mutter in 1996. They disrupt aggregation, reduce aspartimide formation and thus help improving yield in peptide synthesis of difficult and long sequences. In the invention paper also Cysteine based derivatives have been described, but never employed as building blocks so far.

➔ Serine and Threonine based Pseudoprolines are available now for reduced price!

➔ New: Cysteine based Pseudoprolines:

Now this technology is also available with Cysteine residues, as the corresponding 2,4-dimethoxyphenyl-pseudothiaproline is compatible with standard Fmoc/tBu protocols.

Cysteine based pseudoprolines are more stable than the corresponding oxazolidines of Serine and Threonine. Depending on the residues they are stable towards acid treatment or can be cleaved in standard Fmoc/tBu protocols with high concentration of TFA in DCM. We offer both dimethyl and 2,4-dimethoxyphenyl thioprolines to give the synthetic chemist the choice for different kinds of applications.

➔ Click here to find all available Pseudoproline Building Blocks.

Pseudo-Prolines as a Molecular Hinge: Reversible Induction of cis Amide Bonds into Peptide Backbones; P. Dumy, M. Keller, D. E. Ryan, B. Rohwedder, T. Wöhr and M. Mutter; J Am Chem Soc 1997; 119: 918-925. doi:10.1021/ja962780a
Pseudo-Prolines as a Solubilizing, Structure-Disrupting Protection Technique in Peptide Synthesis; T. Wöhr, F. Wahl, A. Nefzi, B. Rohwedder, T. Sato, X. Sun and M. Mutter; J Am Chem Soc 1996; 118: 9218-9227. doi:10.1021/ja961509q
Total chemical synthesis of the D2 domain of human VEGF receptor 1; V. Goncalves, B. Gautier, F. Huguenot, P. Leproux, C. Garbay, M. Vidal and N. Inguimbert; J Pept Sci 2009; 15: 417-422. doi:10.1002/psc.1133
Efficient synthesis and comparative studies of the arginine and Nω,Nω-dimethylarginine forms of the human nucleolin glycine/arginine rich domain; S. Zahariev, C. Guarnaccia, F. Zanuttin, A. Pintar, G. Esposito, G. Maravić, B. Krust, A. G. Hovanessian and S. Pongor; J Pept Sci 2005; 11: 17-28. doi:10.1002/psc.577
Incorporation of Pseudoproline Derivatives Allows the Facile Synthesis of Human IAPP, a Highly Amyloidogenic and Aggregation-Prone Polypeptide; A. Abedini and D. P. Raleigh; Org Lett 2005; 7: 693-696. doi:10.1021/ol047480+
Expediting the Fmoc solid phase synthesis of long peptides through the application of dimethyloxazolidine dipeptides; P. White, J. W. Keyte, K. Bailey and G. Bloomberg; J Pept Sci 2004; 10: 18-26. doi:10.1002/psc.484
An improved synthetic and purification procedure for the hydrophobic segment of the transmembrane peptide phospholamban; E. K. Tiburu, P. C. Dave, J. F. Vanlerberghe, T. B. Cardon, R. E. Minto and G. A. Lorigan; Anal Biochem 2003; 318: 146-151. doi:http://dx.doi.org/10.1016/S0003-2697(03)00141-6