2419-36-5Relevant academic research and scientific papers
Synthetic minimalistic tryptophan zippers as a chiroptical switch
Haridas,Sadanandan, Sandhya,Dhawan, Sameer,Mishra, Rituraj,Jain, Ishani,Goel, Gaurav,Hu, Yuan,Patel, Sandeep
, p. 1661 - 1669 (2017/02/23)
In this paper, we presented a new design strategy for a peptide-based chiral supramolecular assembly. A series of aryl linked peptides 1a-1f were designed and synthesized. The bis-urea peptides 1a-1c self-assembled into a helical supramolecular arrangement resembling Trp zipper (Trpzip) structures present in proteins. Interestingly, a dihydrogenphosphate anion, upon binding to the assembly, could invert the chirality of the supramolecular assembly which could be reverted to the original by the addition of water. This chiroptical behavior can be repeated several times. Microscopy analysis showed that the supramolecular helices were assembled to form spheres. In addition to that, we also found that the handedness of supramolecular chirality is dependent on the position of Trp residues on the aromatic scaffold. Both left and right handed helical supramolecular arrangements were obtained by placing l-Trp residues at different positions on the aromatic core. The unprecedented Trpzip in these designed small peptidomimetics will stimulate more work in the area of peptide-based assemblies.
Urea-cored peptides for anion binding and vesicle formation
Bhardwaj, Ishanki,Sapra, Rachit,Haridas
, p. 184 - 197 (2018/05/09)
Urea and urea-triazole cored peptides were synthesized and characterized. These compounds were analyzed for their potency to sense anions such as F-, Cl-, Br-, I-, H2PO4 - and HSO4 - by UV-
HMDO-promoted peptide and protein synthesis in ionic liquids
Duan, Jianli,Sun, Yao,Chen, Hao,Qiu, Guofu,Zhou, Haibing,Tang, Ting,Deng, Zixin,Hong, Xuechuan
, p. 7013 - 7022 (2013/08/23)
Hexamethyldisiloxane (HMDO) has been developed to efficiently promote the metal-free direct coupling of an amino function of one cysteine-free peptide or protein and a C-terminal thioester of the second peptide in ionic liquids. The amide-coupling reaction proceeds smoothly under mild conditions to afford the corresponding products in good to excellent yields (63-94%). Peptide couplings were also achieved using in-situ-generated thioesters by the thioesterification of oxo esters.
Three types of induced tryptophan optical activity compared in model dipeptides: Theory and experiment
Hudecová, Jana,Horní?ek, Jan,Budě?ínsky, Milo?,?ebestík, Jaroslav,?afa?ík, Martin,Zhang, Ge,Keiderling, Timothy A.,Bou?, Petr
experimental part, p. 2748 - 2760 (2012/10/08)
The tryptophan (Trp) aromatic residue in chiral matrices often exhibits a large optical activity and thus provides valuable structural information. However, it can also obscure spectral contributions from other peptide parts. To better understand the indu
Metal-free direct amidation of peptidyl thiol esters with α-amino acid esters
Chen, Hao,He, Maomao,Wang, Yaya,Zhai, Linhui,Cui, Yongbo,Li, Yangyan,Lee, Yan,Zhou, Haibing,Hong, Xuechuan,Deng, Zixin
, p. 2723 - 2726 (2011/11/06)
Metal-free direct amidation of peptidyl thiol esters with α-amino acid esters in the presence of bis(trimethylsilyl) acetamide (BSA) has been developed. This general method provides convenient access to N-protected peptides in good yields under mild condi
Simple synthesis of 1,3,4,5a,6,10b,11,11a-octahydro-2H-pyrazino[1′,2′:1,5]pyrrolo[2, 3-b]indole derivatives based on 1-hydroxyindole chemistry
Fukui, Yoshikazu,Somei, Masanori
, p. 2055 - 2057 (2007/10/03)
3-Substituted (3S,6S)-6-(1-hydroxyindol-3-ylmethyl)-2,5-piperazinediones are prepared for the first time. They are shown to be suitable intermediates for the synthesis of 3,10b-disubstituted (3S,5aR,10bS,11as)-1,3,4,5a,6,10b,11, 11a-octahydro-2H-pyrazino[
