Stabilization of Azapeptides by N-amide center dot center dot center dot H-N-amide Hydrogen Bonds
| Title | Stabilization of Azapeptides by N-amide center dot center dot center dot H-N-amide Hydrogen Bonds |
| Publication Type | Journal Article |
| Year of Publication | 2021 |
| Authors | Baruah, K, Sahariah, B, Sakpal, SS, Deka, JKishore Ra, Bar, AKumar, Bagchi, S, Sarma, BKanta |
| Journal | Organic Letters |
| Volume | 23 |
| Issue | 13 |
| Pagination | 4949-4954 |
| Date Published | JUL |
| Type of Article | Article |
| ISSN | 1523-7060 |
| Abstract | An unusual N-amide center dot center dot center dot H-Namide hydrogen bond (HB) was previously proposed to stabilize the azapeptide beta-turns. Herein we provide experimental evidence for the N-amide center dot center dot center dot 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 N-amide center dot center dot center dot H-Namide HBs can have stabilizing contributions even in short azapeptides that cannot fold to form beta-turns. |
| DOI | 10.1021/acs.orglett.1c01111 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 6.005 |
Divison category:
Physical and Materials Chemistry
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