1129527-34-9Relevant academic research and scientific papers
A synthetic zipper peptide motif orchestrated via co-operative interplay of hydrogen bonding, aromatic stacking, and backbone chirality
Nair, Roshna V.,Kheria, Sanjeev,Rayavarapu, Suresh,Kotmale, Amol S.,Jagadeesh, Bharatam,Gonnade, Rajesh G.,Puranik, Vedavati G.,Rajamohanan, Pattuparambil R.,Sanjayan, Gangadhar J.
supporting information, p. 11477 - 11480 (2013/09/02)
Here, we report on a new class of synthetic zipper peptide which assumes its three-dimensional zipper-like structure via a co-operative interplay of hydrogen bonding, aromatic stacking, and backbone chirality. Structural studies carried out in both solid- and solution-state confirmed the zipper-like structural architecture assumed by the synthetic peptide which makes use of unusually remote inter-residual hydrogen-bonding and aromatic stacking interactions to attain its shape. The effect of chirality modulation and the extent of noncovalent forces in the structure stabilization have also been comprehensively explored via single-crystal X-ray diffraction and solution-state NMR studies. The results highlight the utility of noncovalent forces in engineering complex synthetic molecules with intriguing structural architectures.
First total synthesis of (-)-Circumdatin H, a novel mitochondrial NADH Oxidase inhibitor
Bose, D. Subhas,Chary, M. Venu
experimental part, p. 643 - 650 (2010/04/30)
An efficient and highly convergent synthesis of the mitochondrial NADH oxidase inhibitor (-)-circumdatin H is described. The strategy employs the intramolecular Eguchi aza-Wittig protocol as a key step to install the crucial central core BC ring system, leading to the first total synthesis of the target molecule. Georg Thieme Verlag Stuttgart · New York.
Total synthesis of asperlicin C, circumdatin F, demethylbenzomalvin A, demethoxycircumdatin H, sclerotigenin, and other fused quinazolinones
Tseng, Ming-Chung,Yang, Huei-Yun,Chu, Yen-Ho
experimental part, p. 419 - 427 (2010/02/16)
Using scandium triflate and microwaves, the direct double dehydrocyclization of anthranilate-containing tripeptides was achieved, affording the total syntheses of (i) quinazolino[3,2-a]benzodiazepinediones (1a-f), (ii) diazepino[2,1-b]quinazolinediones (2a-e), and (iii) pyrazino[2,1-b]quinazolinediones (3a-e) with good overall isolated yields (23-43%, 37-47% and 31-56%, respectively). Among the quinazolino[3,2-a] benzodiazepinediones synthesized, 1a (sclerotigenin), 1b (circumdatin F), and 1f (asperlicin C) are natural products.
Tin triflate-mediated total synthesis of circumdatin F, sclerotigenin, asperlicin C, and other quinazolino[3,2-a][1,4]benzodiazepines
Tseng, Ming-Chung,Lai, Chi-Yu,Chu, Yu-Wan,Chu, Yen-Ho
supporting information; experimental part, p. 445 - 447 (2009/05/06)
Using tin triflate, as an effective Lewis acid, and microwaves, direct double cyclizations of bis(anthranilate)-containing tripeptide precursors to afford the total syntheses of 7-substituted quinazolino[3,2-a][1,4] benzodiazepinediones (1a-f), including natural products circumdatin F (1a), sclerotigenin (1b), and asperlicin C (1c), were achieved with good overall isolated yields (23-62%). The Royal Society of Chemistry.
