284688-79-5Relevant academic research and scientific papers
Synthesis of tripeptides containing a very crowded α,α- disubstituted glycine with pyridine rings by solid-phase Ugi reaction
Hanyu, Masayuki,Murashima, Takashi,Miyazawa, Toshifumi,Yamada, Takashi
, p. 8871 - 8874 (2004)
Tripeptides containing a novel α,α-disubstituted glycine with two pyridine rings, α,α-di(2-pyridyl)glycine (2Dpy), were synthesized by the solid-phase Ugi reaction using di(2-pyridyl)methanimine attached directly to a Rink amide resin. Thereby, yields of the tripeptides, Z-AA1-2Dpy-AA3-OMe (AA1 and AA3 = Gly or Aib), were markedly improved, compared with yields by the solution method.
A novel intramolecular hydrogen bonding between a side-chain pyridine ring and an amide hydrogen of the peptide backbone in tripeptides containing the new amino acid, α,α-di(2-pyridyl)glycine
Yamada, Takashi,Ichino, Tomoyuki,Hanyu, Masayuki,Ninomiya, Daisuke,Yanagihara, Ryoji,Miyazawa, Toshifumi,Murashima, Takashi
, p. 2335 - 2339 (2004)
Four tripeptides (Z-AA1-Dpy-AA3-OMe; AA1 AA3 = Gly, Aib) containing a novel amino acid, α,α-di(2- pyridyl)glycine (2Dpy), were synthesized by the modified Ugi reaction. NMR analysis clearly indicated that the 2Dpy-containing tripeptides except the peptide in which AA1, AA3 = Aib, adopt a unique conformation with two intramolecular hydrogen bonds between 2Dpy-NH and a pyridine nitrogen and between AA3-NH and another pyridine nitrogen. This conformation has so far not been reported. On the other hand, the peptide Z-Aib-2Dpy-Aib-OMe probably adopts a β-turn structure which is stabilized by two intramolecular hydrogen bonds between 2Dpy-NH and a pyridine nitrogen and between AA3-NH and the C=O of the Z group.
