Stabilization of Azapeptides by Namide···H–Namide Hydrogen Bonds

Baruah, Kalpita; Sahariah, Biswajit; Sakpal, Sushil; Rai Deka, Jugal Kishore; Bar, Arun Kumar; Bagchi, Sayan; Sarma, Bani Kanta

dc.contributor.advisor	Bagchi, Sayan
dc.contributor.author	Baruah, Kalpita
dc.contributor.author	Sahariah, Biswajit
dc.contributor.author	Sakpal, Sushil
dc.contributor.author	Rai Deka, Jugal Kishore
dc.contributor.author	Bar, Arun Kumar
dc.contributor.author	Bagchi, Sayan
dc.contributor.author	Sarma, Bani Kanta
dc.date.accessioned	2023-10-10T06:05:33Z
dc.date.available	2023-10-10T06:05:33Z
dc.date.issued	2021-06-01
dc.identifier.other	https://doi.org/10.1021/acs.orglett.1c01111
dc.identifier.uri	https://hdl.handle.net/20.500.12252/6250
dc.description.abstract	An unusual Namide···H–Namide hydrogen bond (HB) was previously proposed to stabilize the azapeptide β-turns. Herein we provide experimental evidence for the Namide···H–Namide HB and show that this HB endows a stabilization of 1–3 kcal·mol–1 and enforces the trans–cis–trans (t–c–t) and cis–cis–trans (c–c–t) amide bond conformations in azapeptides and N-methyl-azapeptides, respectively. Our results indicate that these Namide···H–Namide HBs can have stabilizing contributions even in short azapeptides that cannot fold to form β-turns.	en
dc.format.extent	6	en
dc.language.iso	en_US	en
dc.publisher	Organic Letters	en
dc.title	Stabilization of Azapeptides by Namide···H–Namide Hydrogen Bonds	en
dc.type	Article	en
local.division.division	Physical and Materials Chemistry Division	en
dc.description.university	--	en