93394-80-0Relevant articles and documents
Expressed Protein Ligation without Intein
Kratch, Kaci C.,Leeuwon, Sunshine Z.,Liu, Wenshe Ray,Morse, Jared S.,Qiao, Yuchen,Wang, Wesley Wei,Wang, Xiaoyan Aria,Xu, Shiqing,Yu, Ge
, p. 7047 - 7054 (2020)
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
Electrophilic S-trifluoromethylation of cysteine side chains in α- and β-peptides: Isolation of trifluoromethylated sandostatin (octreotide) derivatives
Caponea, Stefania,Kieltschb, Iris,Floegela, Oliver,Lelaisa, Gerald,Togni, Antonio,Seebach, Dieter
experimental part, p. 2035 - 2056 (2009/02/08)
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.
Cystinophanes, a novel family of aromatic-bridged cystine cyclic peptides: Synthesis, crystal structure, molecular recognition, and conformational studies
Ranganathan, Darshan,Haridas,Karle, Isabella L.
, p. 2695 - 2702 (2007/10/03)
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
