Journal of Organic Chemistry p. 2018 - 2031 (2017)
Update date:2022-08-29
Topics:
Thodupunuri, Prashanth
Katukuri, Sirisha
Ramakrishna, Kallaganti V. S.
Sharma, Gangavaram V. M.
Kunwar, Ajit C.
Sarma, Akella V. S.
Hofmann, Hans-J?rg
Present study describes the synthesis and conformational analysis of β-peptides from C-linked carbo-β-amino acids [β-Caa(l)] with a d-lyxo furanoside side chain and β-hGly in 1:1 alternation. NMR and CD investigations on peptides with an (S)-β-Caa(l) monomer at the N-terminus revealed a right-handed 10/12-mixed helix. An unprecedented solvent-directed "switch" both in helical pattern and handedness was observed when the sequence begins with a β-hGly residue instead of a (S)-β-Caa(l) constituent. NMR studies on these peptides in chloroform indicated a left-handed 10/12-helix, while the CD spectrum in methanol inferred a right-handed secondary structure. The NMR data for these peptides in CD3OH showed the presence of a right-handed 12/10-helix. NMR investigations in acetonitrile indicated the coexistence of both helix types. Quantum chemical studies predicted a small energy difference of 0.3 kcal/mol between the two helix types, which may explain the possibility of solvent influence. Examples for a solvent-directed switch of both the H-bonding pattern and the handedness of foldamer helices are rare so far. A comparable solvent effect was not found in the corresponding peptides with (R)-β-Caa(l) residues, where right-handed 12/10-helices are predominating.
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Doi:10.1111/cbdd.12416
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