319-61-9

Basic information

• Product Name: (S)-1-(trifluoroacetyl)pyrrolidine-2-carboxylic acid
• CAS NO: 319-61-9
• Molecular Weight: 211.141
• Mol File: 319-61-9.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (S)-1-(trifluoroacetyl)pyrrolidine-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-(trifluoroacetyl)pyrrolidine-2-carboxylic acid(319-61-9)
• EPA Substance Registry System: (S)-1-(trifluoroacetyl)pyrrolidine-2-carboxylic acid(319-61-9)

Safety Data

• Hazardous Substances Data: 319-61-9(Hazardous Substances Data)

Upstream product

• 383-63-1 ethyl trifluoroacetate, 
• 147-85-3 L-proline 
• 16652-71-4 benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride 
• 407-25-0 trifluoroacetic anhydride 

Downstream Products

• 36724-68-2 (S)-N-trifluoroacetylproline acid chloride 
• 97589-54-3 (S)-1-(2-benzoylpyrrolidin-1-yl)-2,2,2-trifluoroethan-1-one 
• 119580-41-5 (S)-(+)-2-(trifluoromethyl)pyrrolidine 
• 482-20-2 (S)-(+)-tylophorine 
• 122502-83-4 (+/-)-2-(2,5-dimethoxy-2-methylbenzoyl)-1-(trifluoroacetyl)pyrrolidine 
• 122502-84-5 1-[2-(2,5-Dihydroxy-4-methyl-benzoyl)-pyrrolidin-1-yl]-2,2,2-trifluoro-ethanone 
• 910618-48-3 α-(2,5-dimethoxy-4-methylphenyl)-2-pyrrolidinemethanol 
• 223769-31-1 (S)-1-(2,2,2-Trifluoro-acetyl)-pyrrolidine-2-carboxylic acid diphenylamide 
• 132139-15-2 (S)-N,N-diphenyl-2-pyrrolidinecarboxamide 
• 223769-30-0 (S)-N,N-diphenyl-2-pyrrolidinemethanamine 
• 3847-66-3 (S)-2-anilinocarbonyl-1-trifluoroacetylpyrrolidine 

Relevant articles and documents

Trifluoroacetylation of amino acids and peptides under neutral conditions.

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TFA-protected α-amino acid N-hydroxysuccinimide ester: Application for inter- And intramolecular acylation

The utilization of N-trifluoroacetyl (TFA)-α-amino acid N-hydroxysuccinimide ester (OSu) derivatives, a promising acylating agent with high storage stability, is reported for Friedel-Crafts acylation into arenes and N-heterocycles. The reaction between TF

Modulating hydrogen-bond basicity within the context of protein-ligand binding: A case study with thrombin inhibitors that?reveals a dominating role for desolvation

Understanding subtle aspects of hydrogen bonding is a challenging but crucial task to improve our ability to design ligands with high affinity for protein hosts. To gain a deeper understanding of these aspects, we investigated a series of thrombin inhibitors in which the basicity of the ligand's group that accepts an H-bond from Gly216 was modulated via bioisosterism; e.g., a C=O acceptor was made electron deficient or rich via bioisosteric replacements of the adjacent moiety. Although the ligand's binding affinity was anticipated to improve when the H-bond basicity is increased (due to stronger H-bonding with the protein), we herein present data that unexpectedly revealed an opposite trend. This trend was attributed to a dominating role played by desolvation in determining the relative binding affinity. For example, a decrease in the H-bond basicity reduces the desolvation penalty and, as experimentally observed, improves the binding affinity, given that the reduction in the desolvation penalty dominates the change in the net contribution of the ligand's interactions with the protein. The current study, therefore, reveals that desolvation can be a major underlying cause for the apparently counterintuitive structure-activity relationship (SAR) outcomes, and indicates that understanding this factor can improve our ability to predict binding affinity and to design more potent ligands.