16689-13-7Relevant articles and documents
Design, synthesis, and application of enantioselective coupling reagent with a traceless chiral auxiliary
Kolesinska, Beata,Kaminski, Zbigniew J.
supporting information; experimental part, p. 765 - 768 (2009/09/06)
(Chemical Equation Presented) Stable chiral N-triazinylbrucinium tetrafluoroborate enantioselectively activates racemic carboxylic acids yielding enantiomerically enriched amides, esters, and dipeptides with er from 8:92 to 0.5:99.5. Due to the departure
Thermodynamic and (1)H NMR Study of Proton Complex Formation of Histidine-containing Cyclodipeptides in Aqueous Solution
Arena, Giuseppe,Impellizzeri, Giuseppe,Maccarrone, Giuseppe,Pappalardo, Giuseppe,Sciotto, Domenico,Rizzarelli, Enrico
, p. 371 - 376 (2007/10/02)
A thermodynamic and (1)H NMR study of proton complex formation in aqueous solution of some L-histidine-containing cyclic L-dipeptides has been carried out.The enthalpic and entropic changes associated with protonation of the cyclodipeptides, obtained by potentiometric and calorimetric measurements, together with the (1)H NMR data and NOESY experiments, enable the role played by non-covalent interactions in proton complex formation to be assessed.In addition, a comparison with c(Gly-His) permits the influence of side-chain residues on the conformation of protonated species to be observed.
The Cyclic Dipeptide cyclo as a Catalyst for Asymmetric Addition of Hydrogen Cyanide to Aldehydes
Tanaka, Kenzo,Mori, Atsunori,Inoue, Shohei
, p. 181 - 185 (2007/10/02)
cyclo (cyclo, 1) catalyzes the addition of hydrogen cyanide to benzaldehyde in toluene at -20 deg C to afford (R)-mandelonitrile with enantiomeric excess of 97 percent in high yield. cyclo gives (S)-mandelonitrile. cyclo (1) exhibits a broad substrate specificity, and a variety of aldehydes (3a-r) such as m-methoxybenzaldehyde (3c), 6-methoxy-2-naphthaldehyde (3k), and isobutyraldehyde (3o) similarly afforded the corresponding cyanohydrins with high enantiopurities (97 percent ee for 3c, 93 percent ee for 3k, 71 percent ee for 3o). (R)-Mandelonitrile thus obtained was successfully converted to various chiral synthons such as mandelic acid (7), methyl mandelate (8), and 2-amino-1-phenylethanol (9) without any racemization.