Tfm-PsiPro-OBn (S,S)

Chemical name: (2S,4S)-4-Trifluoromethyl-pseudoproline-benzyl ester // Synonyms: (2S,4S)-benzyl 2-(trifluoromethyl)oxazolidine-4-carboxylate

Product code:HAA2770
CAS No. :1228376-92-8
Formula:C12H12F3NO3
Molecular weight:175,22 g/mol
Grouped product items
Qty Packing unit Price SKU
250 mg
$398.25
HAA2770.0250
500 mg
$573.75
HAA2770.0500
1 g
$877.50
HAA2770.1000
5 g
$3,375.00
HAA2770.5000
description
The incorporation of trifluoromethyl group carrying building blocks into peptides results in increased chemical and thermal stability, increased resistance to degradation by proteases, and enhanced lipophilicity, i.e. better affinity to lipid membranes. Stabilization of particular conformations and auto-assembly can be induced. Also useful as label for 19F-NMR studies. ?-Trifluoromethyl substituted amino acids are, therefore, very attractive building blocks for the design of biologically active compounds.

references
V. P. Kukhar, V. A. Soloshonok in Fluorine Containing Amino Acids: Synthesis and Properties, Wiley, New York, 1995.

B. Koksch, N. Sewald, H.-J. Hofmann, K. Burger, H.-D. Jakubke, J. Pept. Sci. 1997; 3: 157-167.

a) C. Jaeckel, B. Koksch, Eur. J. Org. Chem. 2005; 4483-4503; b) N. C. Yoder, K. Kumar, Chem. Soc. Rev. 2002; 31: 335-341; c) H. Meng, K. Kumar, J. Am. Chem. Soc. 2007; 129:

15615-15622; d) M. Molteni, C. Pesenti, M. Sani, A. Volonterio, M. Zanda, J. Fluorine Chem. 2004; 125: 1335-1743; e) M. Zanda, New J. Chem. 2004; 28: 1401-1411. f) F. Lazzaro, M.

Crucianelli, F. De Angelis, M. Frigerio, L. Malpezzi, A. Volonteriob, M. Zanda, Tetrahedron: Asymmetry 2004; 15: 889-893.

P. K. Mykhailiuk, S. Afonin, G. V. Palamarchuk, O. V. Shishkin, A. S. Ulrich, I. Komarov, Angew. Chem. Int. Ed. 2008; 47: 5765-5767.

S. L. Grage, U. H. N. Duerr, S. Afonin, P. K. Mikhailiuk, I. V. Komarov, A. S. Ulrich, J. Magn. Reson. 2008; 191: 16-23.

P. K. Mikhailiuk, S. Afonin, A. N. Chernega, E. B. Rusanov, M. O. Platonov, G. G. Dubinina, M. Berditsch, A. S. Ulrich, I. V. Komarov, Angew. Chem. Int. Ed. 2006; 45: 5659-5661.

Convenient Synthesis of N-Terminal Tfm-Dipeptides from Unprotected Enantiopure ?-Tfm-Proline and ?-Tfm-Alanine; Grgory Chaume, Nathalie Lensen, Caroline Caupne, and Thierry

Brigaud; Eur. J. Org. Chem. 2009; 5717-5724.

Concise access to enantiopure (S)- and (R)-?-trifluoromethyl pyroglutamic acids from ethyl trifluoropyruvate-based chiral CF3-oxazolidines (Fox); Grgory Chaume, Marie-Cline Van

Severen, Louis Ricard, Thierry Brigaud; J. Fluorine Chem. 2008; 129: 1104-1109.

Synthesis of 2-Trifluoromethyl-1,3-oxazolidines as Hydrolytically Stable Pseudoprolines; Grgory Chaume, Olivier Barbeau, Philippe Lesot, and Thierry Brigaud; J. Org. Chem. 2010;

75: 4135-4145.

Straightforward Synthesis of (S)- and (R)-?-Trifluoromethyl Proline from Chiral Oxazolidines Derived from Ethyl Trifluoropyruvate; Grgory Chaume, Marie-Cline Van Severen, Sinisa

Marinkovic, and Thierry Brigaud; Org. Lett., 2006; 8(26): 6123-6126.

Iodocyclization of Chiral CF3-Allylmorpholinones: A Versatile Strategy for the Synthesis of Enantiopure ?-Tfm-Prolines and ?-Tfm-Dihydroxyprolines; Caroline Caupne, Grgory

Chaume, Louis Ricard, and Thierry Brigaud; Org. Lett. 2009; 11 (1): 209-212.

Julien Simon, Thi Thuan Nguyen, Evelyne Chelain, Nathalie Lensen, Julien Pytkowicz, Grgory Chaume, Thierry Brigaud in press Tetrahedron: Asymmetry 2011.

doi:10.1016/j.tetasy.2011.01.007.

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