93394-80-0

Upstream product

• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 32854-09-4 L-cystine dimethyl ester dihydrochloride 
• 1069-29-0 L-cystine dimethyl ester 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 3674-06-4 Boc-Phe-ONSu 
• 77826-55-2 N,N'-bis(tert-butoxy)carbonyl-L-cystine dimethyl ester 
• 10389-65-8 di-t-butoxycarbonyl-L-cystine 
• 63-91-2 L-phenylalanine 

Downstream Products

• 1110723-26-6 methyl (R)-2-{(S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanamido}-3-[(trifluoromethyl)sulfanyl]propanoate 
• 461638-99-3 (S)-tert-butyl (1-oxo-3-phenyl-1-(prop-2-yn-1-ylamino)propan-2-yl)carbamate 
• 93394-81-1 bis(phenylalanyl)cystine dimethyl ester 

Relevant academic research and scientific papers

Expressed Protein Ligation without Intein

Proteins with a functionalized C-terminus such as a C-terminal thioester are key to the synthesis of larger proteins via expressed protein ligation. They are usually made by recombinant fusion to intein. Although powerful, the intein fusion approach suffe

18F-Trifluoromethylation of Unmodified Peptides with 5-18F-(Trifluoromethyl)dibenzothiophenium Trifluoromethanesulfonate

The 18F-labeling of 5-(trifluoromethyl)-dibenzothiophenium trifluoromethanesulfonate, commonly referred to as the Umemoto reagent, has been accomplished applying a halogen exchange 18F-fluorination with 18F-fluoride, follo

Electrophilic S-trifluoromethylation of cysteine side chains in α- and β-peptides: Isolation of trifluoromethylated sandostatin (octreotide) derivatives

The new electrophilic trifluoromethylating 1-(trifluoromethyl)-benziodoxole reagents A and B (Scheme 1) have been used to selectively attach CF3 groups to the S-atom of cysteine side chains of α- and β-peptides (up to 13-residues-long; products 7-14). Other functional groups in the substrates (amino, amido, carbamate, carboxylate, hydroxy, phenyl) are not attacked by these soft reagents. Depending on the conditions, the indole ring of a Trp residue may also be trifluoromethylated (in the 2-position). The products are purified by chromatography, and identified by 1H-, 13C-, and 19F-NMR spectroscopy, by CD spectroscopy, and by high-resolution mass spectrometry. The CF3 groups, thus introduced, may be replaced by H (Na/NH3), an overall Cys/Ala conversion. The importance of trifluoromethylations in medicinal chemistry and possible applications of the method (spin-labelling, imaging, PET) are discussed.

Design and synthesis of novel amino acid-bearing macrocyclic calix[4]arenes

A new family of macrocyclic calix[4]arenes (4a-d) potentially capable of chiral recognition were synthesized by incorporating the chirality inducing moieties, bis α-amino acylated polyethylene glycols, or tripeptide bis-Phe Cystine(OMe)2 to the

Cystinophanes, a novel family of aromatic-bridged cystine cyclic peptides: Synthesis, crystal structure, molecular recognition, and conformational studies

A novel family of aromatic-bridged cystine cyclic peptides (cystinophanos) has been synthesized by a single-step procedure involving condensation of 1,3 aromatic (Ph or Pyr unit) dicarbonyl dichloride with either the simple L-cystine dimethyl ester to pro

Oxidative Deblocking of the 4-Methoxybenzyl Thioether Protecting Group: Application to the Directed Synthesis of Poly-cystinyl Peptides

The 4-methoxybenzyl thioether protecting group is deblocked efficiently by oxidation with the homogeneous electron transfer agent tris(4-bromophenyl)ammoniumyl (2.+) leading to the disulfide in high yields.S-(4-methoxybenzyl)cysteine derivatives like 9 in this way can be transformed into the corresponding cystine derivatives like 10 in 90percent yield.Many N and carboxy protecting groups like the Boc and Z group and tert-butyl or benzyl ester functions are stable under the cleavage conditions.On the other hand the 4-methoxybenzyl thioether protecting group is totally unaffected by the conditions for oxidative deblocking of the S-trityl functions by either iodine or rhodanolysis.This opens up new opportunities for the directed synthesis of cystinyl peptides with more than one intra- or interchain disulfide bridge.Application of the new method to the synthesis of a cystine peptide with one intrachain S-S-bridge and a double-chain biscystinyl peptide is reported.