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http://hdl.handle.net/10603/444394
Title: | Understanding the role of noncovalent interactions in the conformational properties of aza peptidomimetics |
Researcher: | Baruah, Kalpita |
Guide(s): | Sarma, Bani Kanta |
Keywords: | Chemistry Chemistry Applied Physical Sciences |
University: | Shiv Nadar University |
Completed Date: | 2022 |
Abstract: | In my PhD thesis work, I have studied the conformational properties of azapeptides and azapeptoids in detail and discovered that the ability of the hydrazide nitrogen lone pair to participate in non-covalent interactions greatly influence the conformational properties of these molecules. In the Chapters 2 and 3 of the thesis, from the study of carefully designed azapeptide and N-methyl azapeptide models, I show that an unusual Namide····Hand#8213;Namide hydrogen bond (HB) between the hydrazide nitrogen at (i+2) and the NH hydrogen at the (i+3) positions play crucial roles in the stabilization of azapeptide and#946;-turns. These studies also revealed that these Namide···H Namide HBs can have stabilizing contributions even in short azapeptides that cannot fold to form and#946;-turns.6 In Chapters 4 and 5, I discuss the conformational properties of azapeptoids, chiral azapeptoids and N-methyl-azapeptoids. In these azapeptoid molecules, we discovered an nN and#8594; and#963;*Cand#8213;N noncovalent carbon bonding (C-bonding) interaction between the lone pair of sidechain hydrazide amidic nitrogen atom and the antibonding and#963; (and#963;*) of the backbone Cand#9472;N(CO) bond that enforces trans backbone amide bond geometries in azapeptoids. Further, investigations of other trans-inducing peptoid sidechains revealed that sidechain-backbone non-covalent interaction could provide a general mechanism to stabilize homogenous trans-peptoids, a property essential for peptoid-based bioactive molecules. In conclusion, in this PhD thesis work, I have studied the conformational properties of two azapeptidomimetics, azapeptide and azapeptoid and established the roles of Namide····Hand#8213;Namide HB and nN and#8594; and#963;*Cand#8213;N noncovalent C-bonding interactions, respectively, in their conformational rigidity. Further, we proposed a sidechain-backbone noncovalent interaction mechanism to design homogeneous trans-peptoids, which should inspire further works in this direction. newline |
Pagination: | |
URI: | http://hdl.handle.net/10603/444394 |
Appears in Departments: | Department of Chemistry |
Files in This Item:
File | Description | Size | Format | |
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01_title.pdf | Attached File | 43.55 kB | Adobe PDF | View/Open |
02_prelim pages.pdf | 1.23 MB | Adobe PDF | View/Open | |
03_content.pdf | 130.64 kB | Adobe PDF | View/Open | |
04_chapter 1.pdf | 619.03 kB | Adobe PDF | View/Open | |
05_chapter 2.pdf | 2.38 MB | Adobe PDF | View/Open | |
06_chapter 3.pdf | 2.12 MB | Adobe PDF | View/Open | |
07_chapter 4.pdf | 1.91 MB | Adobe PDF | View/Open | |
08_chapter 5.pdf | 2.01 MB | Adobe PDF | View/Open | |
09_annexures.pdf | 5.89 MB | Adobe PDF | View/Open | |
80_recommendation.pdf | 348.34 kB | Adobe PDF | View/Open |
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