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Chemical name: (S)-3-(N-(9-Fluorenylmethyloxycarbonyl)-beta-trityl-L-asparaginyl)-2-(2,4-dimethoxphenyl)thiazolidine-4-carboxylic acid // Synonyms: Fmoc-L-Asn(Trt)-L-Cys[PSI(Dmbz,H)pro]-OH, Fmoc-Asn(Trt)-2,4-dimethoxybenzyl-pseudothiaproline
|Molecular weight:||847.97 g/mol|
Cysteine based Pseudoproline. The 2,4-dimethoxyphenyl-pseudothiaproline is compatible with standard Fmoc/tBu protocols and can be cleaved with 80% TFA in DCM.
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, M. Mutter; J. Am. Chem. Soc. 1997; 119: 918-925. https://doi.org/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, M. Mutter; J. Am. Chem. Soc. 1996; 118: 9218-9227. https://doi.org/10.1021/ja961509q.
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. https://doi.org/10.1002/psc.484
Total chemical synthesis of the D2 domain of human VEGF receptor 1; V. Goncalves, B. Gautier, F. Huguenot, P. Leproux, C. Garbay, M. Vidal, N. Inguimbert; J. Pept. Sci. 2009; 15: 417-422. https://doi.org/10.1002/psc.1133.
Efficient synthesis and comparative studies of the arginine and Nomega,Nomega-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, S. Pongor; J. Pept. Sci. 2005; 11: 17-28. https://doi.org/10.1002/psc.577.
Incorporation of Pseudoproline Derivatives Allows the Facile Synthesis of Human IAPP, a Highly Amyloidogenic and Aggregation-Prone Polypeptide; A. Abedini, D. P. Raleigh; Org. Lett. 2005; 7(4): 693-696. https://doi.org/10.1021/ol047480+.
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, G. A. Lorigan; Anal. Biochem. 2003; 138(1): 146-151. https://doi.org/10.1016/S0003-2697(03)00141-6.
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