78212-13-2Relevant academic research and scientific papers
α-Methylphenacyl thioesters as convenient thioacid precursors
Hatanaka, Toru,Yuki, Ryosuke,Saito, Ryota,Sasaki, Kaname
supporting information, p. 10589 - 10592 (2016/11/30)
α-Methylphenacyl (Mpa) thioesters are described as precursors of thioacids. Mpa thioesters are accessible via the condensation of carboxylic acids and phenacyl thiol, which is easily prepared without column chromatography. The Mpa thioesters are selectively deprotected by reduction with zinc dust in the presence of conventional thioacid protecting groups. In addition, the Mpa group exhibits orthogonal reactivity to the Boc group. These features are expected to facilitate the preparation of complex thioacids, including those in peptides.
T3P (propylphosphonic anhydride) mediated conversion of N α-protected amino/peptide acids into thioacids
Madhu, Chilakapati,Basavaprabhu,Vishwanatha,Sureshbabu, Vommina V.
experimental part, p. 1406 - 1409 (2012/03/27)
A general, mild and an efficient protocol, which makes use of T3P as an acid activator for the synthesis of Nα-protected amino/peptide thioacids from corresponding acids in the presence of finely ground Na 2S as hydrosulfide ion donor is described. The protocol employed significantly increases the overall efficiency as the yield, reaction duration and purity of even sterically hindered amino acids.
Thioglycine and l-thiovaline: Biologically active H2S-donors
Zhou, Zongmin,Von Wantoch Rekowski, Margarete,Coletta, Ciro,Szabo, Csaba,Bucci, Mariarosaria,Cirino, Giuseppe,Topouzis, Stavros,Papapetropoulos, Andreas,Giannis, Athanassios
scheme or table, p. 2675 - 2678 (2012/05/31)
Thioglycine and l-thiovaline are stable under acidic and basic conditions but in the presence of bicarbonate they liberate the gasotransmitter H 2S. In cells both thioamino acids were proven to enhance cGMP formation and promote vasorelaxation in mouse aortic rings. Given that H 2S is known to lower arterial hypertension, reduce oxidative stress and exhibit cardioprotective effects in preclinical models, H2S donors hold promise as novel treatments for cardiovascular diseases.
Assembly/disassembly of drug conjugates using imide ligation
Mhidia, Reda,Beziere, Nicolas,Blanpain, Annick,Pommery, Nicole,Melnyk, Oleg
supporting information; experimental part, p. 3982 - 3985 (2010/11/02)
A strategy is described that allows the easy assembly and controlled disassembly of drug conjugates. Imide ligation, that is, the reaction of a peptide thioacid with an azidoformate, is used for conjugate assembly. The imide bond participates also with an endopeptidase-triggered cyclization-based disassembly mechanism.
Design and synthesis of novel bis(l-amino acid) ester prodrugs of 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA) with improved anti-HBV activity
Fu, Xiaozhong,Jiang, Saihong,Li, Chuan,Xin, Jian,Yang, Yushe,Ji, Ruyun
, p. 465 - 470 (2007/10/03)
A series of novel bis(l-amino acid) ester prodrugs of 9-[2-(phosphonomethoxy)ethyl] adenine (PMEA) was synthesized and their anti-HBV activity was evaluated in HepG 2 2.2.15 cells. Compounds 11, 12, 21, 22, 26, and 27 demonstrated more potent anti-HBV act
Use of BOP-Cl in the presence of Boc-amino monothioacids for the thioacylation of iminoacid residues
Le, Hoang-Thanh,Gallard, Jean-Francois,Mayer, Michel,Guittet, Eric,Michelot, Robert
, p. 2201 - 2209 (2007/10/03)
BOP-Cl was found to be an efficient coupling reagent for the introduction of thiopeptide bonds on imino acid residues (Pro, Sar). Boc-amino monothioacids were coupled at moderate temperature (0°C-RT) with fair yields and with retained optical purity. The
