1492-83-7

Usage

Uses

Used in Pharmaceutical Industry:
N,N'-Bis(trifluoroacetyl)-L-cystine dimethyl ester is used as an intermediate in the synthesis of N-trifluoroacetyl dipeptides for enhancing the stability and bioavailability of these therapeutic agents. The trifluoroacetyl group provides a protective function, shielding the peptide bond from enzymatic degradation, thus improving the half-life and efficacy of the resulting dipeptides in the body.
Used in Chemical Synthesis:
In the field of chemical synthesis, N,N'-Bis(trifluoroacetyl)-L-cystine dimethyl ester serves as a versatile building block for the creation of various complex molecules. Its unique structure allows for further functionalization and modification, making it a valuable component in the development of new drugs, agrochemicals, and other specialty chemicals.
Used in Research and Development:
N,N'-Bis(trifluoroacetyl)-L-cystine dimethyl ester is also utilized in research and development laboratories for studying the properties and reactivity of trifluoroacetyl-protected peptides. N,N'-Bis(trifluoroacetyl)-L-cystine dimethyl ester can be used to investigate the effects of trifluoroacetyl protection on peptide conformation, stability, and interactions with other biomolecules, providing valuable insights for the design of novel therapeutic agents and materials.

Upstream product

• 32854-09-4 L-cystine dimethyl ester dihydrochloride 
• 407-25-0 trifluoroacetic anhydride 
• 3108-67-6 S-benzyl-N-trifluoroacetyl-L-cysteine methyl ester 
• 329-52-2 S-benzyl-N-trifluoroacetyl-L-cysteine 

Downstream Products

• 26527-25-3 (R)-3-[(R)-2-Methoxycarbonyl-2-(2,2,2-trifluoro-acetylamino)-ethylsulfanyl]-2-(2,2,2-trifluoro-acetylamino)-propionic acid methyl ester 
• 110-81-6 Diethyl disulfide 
• 13003-31-1 ethyl trifluoromethyl sulphide 
• 26527-25-3 N,N'-bis(trifluoroacetyl)-L-lanthionine dimethyl ester 

Relevant academic research and scientific papers

Synthesis of S-trifluoromethyl-containing α-amino acids from sodium trifluoromethanesulfinate and dithio-amino acids

N-Protonated or N-acetylated dimethyl cystinates and homocystinates react with sodium trifluoromethanesulfinate and t-butyl hydroperoxide to yield the corresponding derivatives of methyl S-trifluoromethyl cysteinate and homocysteinate in a stereospecific manner.Methyl S-trifluoromethyl-N-acetyl cysteinate and homocysteinate are readily saponified, without racemization, by sodium hydrogen carbonate in a water/methanol mixture.

Triply bridged (1,3,5) cyclophanes from cystine and lanthionine linkers-a comparison

The condensation of benzene 1,3,5-tricarbonylchloride with cystine-di-Me [H2N-CH(COOMe)-CH2-S-S-CH2-CH(COOMe)-NH 2] yielded triply bridged (1,3,5) cyclophane 1, which was shown by detailed spectral studies and molecular orbital calculations to have a D3 symmetry with conformationally identical linkers and a spherical topology. In sharp contrast, the (1,3,5) cyclophane 2 from the rarely studied lanthionine di-Me [H2N-CH(COOMe)-CH2-S-CH2-CH(COOMe)-NH 2], showed only a equatorial twofold symmetry. This work highlights the special properties of the -S-S- bridge in cystine, which makes it an exceptional synthon in nature and organic synthesis.

Synthetic Uses of Thio- and Selenoesters of Trifluoromethylated Acids. 1. Preparation of Trifluoromethyl Sulfides and Selenides

Trifluorothioacetates (CF3CO-S-R, from (CF3CO)2O and thiols) as well as trifluoromethanethio-or trifluoromethaneselenosulfonates (CF3SO2-Y-R; Y = S, Se; from CF3SO2Na, RYYR, and Br2) can be formally decarbonylated or desulfonylated, respectively, provided that they are photolyzed at 40°C in the presence of 1 equiv of the corresponding disulfide or diselenide. Trifluoromethyl sulfides or selenides are obtained, and the added disulfide (or diselenide) is recovered after reaction. In such a way, S-(trifluoromethyl)cysteine derivatives can be obtained.

Fluorination of sulfur-containing amino acids: Reaction of xenon difluoride with cysteine derivatives

The reaction of XeF2 with cysteine derivatives RSCH2CH(NHR)COOR, i.e., S-benzyl-N-trifluoroacetyl-L-cysteine methyl ester, S-benzyl-N-carbobenzoxy-L-cysteine p-nitrophenyl ester, and S-methyl-N-trifluoroacetyl-L-cysteine methyl ester is described.The fluorinated products PhCHFSCH2CH(NHR)COOR, PhCH2SCHFCH(NHR)COOR, and FCH2SCH2CH(NHR)COOR were identified by 1H and 19F nuclear magnetic resonance spectroscopy.PhCH2SCHFCH(NHR)COOR loses HF within 24 hours to give Z- and E-PhCH2SCH=C(NHR)COOR.If the reaction with XeF2 is carried out in the presence of moisture the sulfoxide RS(O)CH2CH(NHR)COOR and sulfone RSO2CH2CH(NHR)COOR are produced.