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δ ‐Peptide Analogues of Pyranosyl‐RNA, Part 2, Nucleo‐ δ ‐peptides Derived from Conformationally Constrained Nucleo‐ δ ‐amino Acids: NMR Study of the Duplex Formed by Self‐pairing of the (1′ S ,2′ S ,4′ S )‐(phba)‐Nucleo‐ δ ‐peptide‐(AATAT)
Author(s) -
Schwalbe Harald,
Wermuth Jochen,
Richter Christian,
Szalma Sandor,
Eschenmoser Albert,
Quinkert Gerhard
Publication year - 2000
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(20000607)83:6<1079::aid-hlca1079>3.0.co;2-w
Subject(s) - chemistry , duplex (building) , antiparallel (mathematics) , base pair , stereochemistry , nucleobase , crystallography , dna , biochemistry , physics , quantum mechanics , magnetic field
δ ‐Peptides of the type described in this series are analogues of pyranosyl‐RNAs with respect to their capability of base pairing in the Watson‐Crick mode. An NMR‐based conformational analysis of the title duplex at various levels of sophistication has been carried out: at the level of qualitative conformational analysis, at that of quantitative conformational analysis, and at that of structure calculation using MD search of torsion‐angle space. The duplex formed has an antiparallel arrangement of two complementary strands and is stabilized by Watson‐Crick base pairing, as well as by interstrand π ‐ π base stacking, dangling‐end nucleobase interaction included.