Fmoc-L-Glu(tBu)-L-Cys[PSI(Dmp,H)pro]-OH

Chemical name: (S)-3-(N-(9-Fluorenylmethyloxycarbonyl)-gamma-t-butyl-L-glutamyl)-2-(2,4-dimethoxphenyl)thiazolidine-4-carboxylic acid // Synonyms: Fmoc-L-Glu(tBu)-L-Cys[PSI(Dmbz,H)pro]-OH, Fmoc-Glu(tBu)-2,4-dimethoxybenzyl-pseudothiaproline

Art-No.:PSI1490
Formula:C36H40N2O9S
Molecular weight:676.78 g/mol
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PSI1490.0000
description
Cysteine based Pseudoproline. The 2,4-dimethoxyphenyl-pseudothiaproline is compatible with standard Fmoc/tBu protocols and can be cleaved with 80% TFA in DCM.

references
Pascal Dumy, Michael Keller, Declan E. Ryan, Barbara Rohwedder, Torsten Wh r, and Manfred Mutter; Pseudo-Prolines as a Molecular Hinge: Reversible Induction of cis Amide Bonds

into Peptide Backbones; J. Am. Chem. Soc. 1997; 119: 918-925.

Torsten Whr, Franck Wahl, Adel Nefzi, Barbara Rohwedder, Tatsunori Sato, Xicheng Sun, and Manfred Mutter; Pseudo-Prolines as a Solubilizing, Structure-Disrupting Protection

Technique in Peptide Synthesis; J. Am. Chem. Soc. 1996; 118: 9218-9227.

Goncalves, V., Gautier, B., Huguenot, F., Leproux, P., Garbay, C., Vidal, M. and Inguimbert, N.; Total chemical synthesis of the D2 domain of human VEGF receptor 1. J. Peptide

Sci. 2009; 15: 417-422. doi: 10.1002/psc.1133.

Zahariev, S., Guarnaccia, C., Zanuttin, F., Pintar, A., Esposito, G., Maravi?, G., Krust, B., Hovanessian, A. G. and Pongor, S.; Efficient synthesis and comparative studies of the

arginine and N?,N?-dimethylarginine forms of the human nucleolin glycine/arginine rich domain. J. Peptide Sci. 2005; 11: 17-28. doi: 10.1002/psc.577.

Andisheh, A., Raleigh, D.P.; Incorporation of Pseudoproline Derivatives Allows the Facile Synthesis of Human IAPP, a Highly Amyloidogenic and Aggregation-Prone Polypeptide; Org.

Lett. 2005; 7(4): 693-696. doi: 10.1021/ol047480+.

White, P., Keyte, J. W., Bailey, K. and Bloomberg, G.; Expediting the Fmoc solid phase synthesis of long peptides through the application of dimethyloxazolidine dipeptides. J.

Peptide Sci. 2004; 10: 18-26. doi: 10.1002/psc.484.

Tiburu, E.K., Dave, P.C., Vanlerberghe, J.F., Cardon, T.B., Minto, R.E., Lorigan, G.A.; An improved synthetic and purification procedure for the hydrophobic segment of the

transmembrane peptide phospholamban. Anal. Biochem. 2003; 318(1): 146-151. doi: 10.1016/S0003-2697(03)00141-6.

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