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Volumn 51, Issue 6, 2012, Pages 1395-1399

Induction of unexpected left-handed helicity by an N-terminal L -amino acid in an otherwise achiral peptide chain

Author keywords

circular dichroism; conformation analysis; foldamers; helical structures; peptides

Indexed keywords

ACHIRAL AMINO ACIDS; CHIRAL AMINO ACIDS; CONFORMATION ANALYSIS; FOLDAMERS; HELICAL STRUCTURES; HELICITIES; L-AMINO ACIDS; L-VALINE; N-TERMINALS; PEPTIDE CHAIN; PROTEINOGENIC AMINO ACIDS;

EID: 84863012106     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201107583     Document Type: Article
Times cited : (77)

References (61)
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    • Pauling's first diagram of an αhelixfamously shows a left-handed helix with D -amino acids; see
    • Pauling's first diagram of an αhelix (, L. Pauling, R. B. Corey, H. R. Branson, Proc. Natl. Acad. Sci. USA 1951, 37, 205-211) famously shows a left-handed helix with D -amino acids; see
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    • For reports of induction of helicity by noncovalent binding to the Nterminus of a dehydropeptide, see
    • Y. Inai, Y. Ishida, K. Tagawa, A. Takaso, T. Hirabayashi, J. Am. Chem. Soc. 2002, 124, 2466-2473. For reports of induction of helicity by noncovalent binding to the Nterminus of a dehydropeptide, see
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    • Inai, Y.1    Ishida, Y.2    Tagawa, K.3    Takaso, A.4    Hirabayashi, T.5
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    • references therein.
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    • A consistent exception is when an L -amino acid finds itself at the C-terminal residue of a peptide ester (see Ref.[9] for example) an effect noted by Schellman (in (Ed.: R. Jaenicke), Elsevier, Amsterdam). The alamethicin fragment Boc-Pro-Aib-Ala-Aib-Ala-OH
    • A consistent exception is when an L -amino acid finds itself at the C-terminal residue of a peptide ester (see Ref.[9] for example) an effect noted by Schellman (, C. Schellman, in Protein Folding (Ed.:, R. Jaenicke,), Elsevier, Amsterdam 1980). The alamethicin fragment Boc-Pro-Aib-Ala-Aib-Ala-OH
    • (1980) Protein Folding
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    • [13d] Left-handed helicity has been observed in related structures in the crystalline state (see, for example
    • [13d] Left-handed helicity has been observed in related structures in the crystalline state (see, for example
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    • The magnitude of the anisochronicity also provides a measure of relative helical conformational preference: see Ref.[8], [10] and.
    • The magnitude of the anisochronicity also provides a measure of relative helical conformational preference: see Ref.[8], [10] and, J. Solà, M. Helliwell, J. Clayden, J. Am. Chem. Soc. 2010, 132, 4548-4549.
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    • A similarly strong dependence of chiroptical properties from the same torsional angle in benzamides was recently observed by Meijer, Palmans, and co-workers in a combined CD/TD-DFT study on supramolecular helical polymers.
    • A similarly strong dependence of chiroptical properties from the same torsional angle in benzamides was recently observed by Meijer, Palmans, and co-workers in a combined CD/TD-DFT study on supramolecular helical polymers:, Y. Nakano, T. Hirose, P. J. M. Stals, E. W. Meijer, A. R. A. Palmans, Chem. Sci. 2012, 3, 148-155.
    • (2012) Chem. Sci. , vol.3 , pp. 148-155
    • Nakano, Y.1    Hirose, T.2    Stals, P.J.M.3    Meijer, E.W.4    Palmans, A.R.A.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.