Concepedia

Preparation and determination of X-ray-crystal and NMR-solution structures of γ2,3,4-peptides

Dieter Seebàch, Meinrad Brenner, Magnus Rueping, W. Bernd Schweizer, Bernhard Jaun

Chemical Communications · 2001 · 97 citations · 4 references

DOI

Concepts

Abstract

(R,R,R)-γ-Amino acids with side chains in the 2-, 3-, and 4-positions, prepared by addition of acyloxazolidinones to a nitroolefin and hydrogenation, have been coupled to γ- tetra-, and γ-hexapeptides which are shown to form (M)-2.614 helices in the crystal state and in MeOH solution.

References

4

Design of Secondary Structures in Unnatural Peptides: Stable Helical γ-Tetra-, Hexa-, and Octapeptides and Consequences of α-Substitution

Stephen Hanessian, Xuehong Luo, Robert Schaum et al. · Journal of the American Chemical Society · 1998 · 268 citations

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γ‐Peptides Forming More Stable Secondary Structures than α‐Peptides: Synthesis and helical NMR‐solution structure of the γ‐hexapeptide analog of H‐(Val‐Ala‐Leu)<sub>2</sub>‐OH

Tobias Hintermann, Karl Gademann, Bernhard Jaun et al. · Helvetica Chimica Acta · 1998 · 217 citations · Full text

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Synthesis and folding preferences of γ-amino acid oligopeptides: stereochemical control in the formation of a reverse turn and a helix

Stephen Hanessian, Xuehong Luo, Robert Schaum · Tetrahedron Letters · 1999 · 86 citations

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Enantioselective Preparation of <i>γ</i> ‐Amino Acids and <i>γ</i> ‐Lactams from Nitro Olefins and Carboxylic Acids, with the Valine‐Derived 4‐Isopropyl‐5,5‐diphenyl‐1,3‐oxazolidin‐2‐one as an Auxiliary

Meinrad Brenner, Dieter Seebàch · Helvetica Chimica Acta · 1999 · 71 citations

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