H-alpha-Tfm-L-Pro-OH

Chemical name: (S)-Trifluoromethylproline // Synonyms: (S)-2-Trifluoromethyl-pyrrolidine-2-carboxylic acid , H-alpha-Tfm-Pro-OH

  • Product code:HAA1945
  • CAS No.:921224-82-0
  • Formula:C6H8F3NO2
  • Molecular weight:183.13 g/mol

Starting at $845.00

Grouped product items
Qty Packing unit Price SKU
250 mg
$845.00
HAA1945.0250
500 mg
$1,332.50
HAA1945.0500
1 g
$1,982.50
HAA1945.1000
description

Building block which can be used for the direct implementation of a trifluoromethylated amino acid (Tfm-Aaa) at the N-terminus of a peptide. The trifluoromethyl group reduces the nucleophilicity of the amino function to a level that no further protection (e.g. by Boc, Fmoc or Z) is necessary.

For the introduction of this Tfm amino acid within the sequence the design of a dipeptide building block is required (Fmoc-Aaa-Tfm-Aaa), which can then be incorporated in a peptide sequence by standard SPPS methodologies. Please consult with our custom synthesis division.


references

Fluorine in Peptide Design and Protein Engineering; C. Jäckel and B. Koksch; Eur J. Org. Chem. 2005; 21: 4483-4503. https://doi.org/10.1002/ejoc.200500205

Conformational properties of peptides incorporating a fluorinated pseudoproline residue; G. Chaume, D. Feytens, G. Chassaing, S. Lavielle, T. Brigaud, E. Miclet; New J. Chem. 2013; 37: 1336-1342. https://doi.org/10.1039/C3NJ41084F

Impact of fluorination on proteolytic stability of peptides in human blood plasma; V. Asante, J. Mortier, H. Schlüter, B. Koksch; Bioorg. Med. Chem. 2013; 21: 3542-3546. https://doi.org/10.1016/j.bmc.2013.03.051.

Fluorinated Proteins: From Design and Synthesis to Structure and Stability; E. N. G. Marsh; Acc. Chem. Res. 2014; 47: 2878-2886. https://doi.org/10.1021/ar500125m

How Cα-Fluoroalkyl Amino Acids and Peptides Interact with Enzymes: Studies Concerning the Influence on Proteolytic Stability, Enzymatic Resolution and Peptide Coupling; R. Smits, B. Koksch; Current Topics in Medicinal Chemistry 2006; 6: 1483-1498. https://doi.org/10.2174/156802606777951055

Approaches to Obtaining Fluorinated α-Amino Acids; J. Moschner, V. Stulberg, R. Fernandes, S. Huhmann, J. Leppkes, B. Koksch; Chem. Rev. 2019; 119: 10718-10801. https://doi.org/10.1021/acs.chemrev.9b00024

Applications of fluorine-containing amino acids for drug design; H. Mei, J. Han, K. D. Klika, K. Izawa, T. Sato, N. A. Meanwell, V. A. Soloshonok; Eur. J. Med. Chem. 2020; 186: 111826. https://doi.org/10.1016/j.ejmech.2019.111826

Fluorinated amino acids: compatibility with native protein structures and effects on protein-protein interactions; M. Salwiczek, E. K. Nyakatura, U. I. M. Gerling, S. Ye, B. Koksch; Chem. Soc. Rev. 2012; 41: 2135-2171. https://doi.org/10.1039/C1CS15241F

Substitution Effect of the Trifluoromethyl Group on the Bioactivity in Medicinal Chemistry: Statistical Analysis and Energy Calculations; A. Abula, Z. Xu, Z. Zhu, C. Peng, Z. Chen, W. Zhu, H. A. Aisa; J. Chem. Inf. Model 2020; https://doi.org/10.1021/acs.jcim.0c00898

Synthesis of an MIF-1 analogue containing enantiopure (S)-alpha-trifluoromethyl-proline and biological evaluation on nociception; I. Jlalia, N. Lensen, G. Chaume, E. Dzhambazova, L. Astasidi, R. Hadjiolova, A. Bocheva, T. Brigaud; Eur J Med Chem 2013; 62: 122-9. https://doi.org/10.1016/j.ejmech.2012.12.041


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