Conformational analysis of 4-amido-2,4-dimethylbutyric acid derivatives

Hoffmann, Reinhard W.; Caturla, Francisco; Lázaro, M. A.; Framery, Éric; Bernabeu, Melania; Valancogne, Ingrid; Montalbetti, Christian

doi:10.1039/a910179i

Cited by 10 publications

(5 citation statements)

References 8 publications

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“…The added torsional degrees of freedom in γ-amino acids , might be expected to promote conformationally disordered chains. Yet, just as for β-peptides, this intuitive view does not hold for the γ-peptides either.…”

Section: The γ-Peptide Family1 γ-Peptide Foldamersmentioning

confidence: 99%

“…316 However, there appears to be no resolution to the question of whether these polymers are helical or conformationally random. 192,320 The added torsional degrees of freedom in γ-amino acids 321,322 might be expected to promote conformationally disordered chains. Yet, just as for β-peptides, this intuitive view does not hold for the γ-peptides either.…”

Section: γ-Peptide Foldamersmentioning

confidence: 99%

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A Field Guide to Foldamers

et al. 2001

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He attended Point Loma Nazarene University in San Diego, CA, where he worked with Professor Victor L. Heasley on the halogenation of unsaturated carbonyl compounds. After receiving his B.A. degree in Chemistry in 1997, he began his graduate career at the University of Illinois with Professor Jeffrey S. Moore. Currently he is in his fifth year investigating solvent effects on the helix−coil transition in oligo(m-phenylene ethynylene) foldamers. Matthew J. Mio (left) was born in Michigan in 1974. He attended the University of Detroit Mercy, where he worked with Professor Kevin. D. Belfield (now at the University of Central Florida) on the synthesis of nonlinear optical chromophores for use in polymeric systems. He graduated with his B.S. degree in Chemistry in 1997. Later that year, he began his graduate career at the University of Illinois at Urbana−Champaign with Professor Jeffrey S. Moore. There, Matt studied the synthesis and solution/ solid-state properties of oligo(m-phenylene ethynylene) foldamers and graduated with his Ph.D. degree in 2001. He then went to the Chemistry Department at Macalester College (St. Paul, MN) as a Mellon Postdoctoral Fellow to study the synthesis of novel CpCo−cyclobutadienyl-bridged cyclophanes with Professor Ronald G. Brisbois. Thomas S. Hughes (right) is currently a postdoctoral fellow in the research group of Professor Jeff Moore at the University of Illinois. He was born in 1970 in Philadelphia, PA, and received his B.S. degree from Temple University in 1991. In 1999 he received his Ph.D. degree from Cornell University, where he worked in the laboratories of Professor Barry Carpenter. He is currently studying the association kinetics of the binding of a helical oligomer to a rodlike guest. He is also investigating the thermodynamics of oligo(phenylene ethynylene) folding using molecular mechanics. Jeffrey S. Moore (second from right) was born in Illinois in 1962. After receiving his B.S. degree in Chemistry from the University of Illinois in 1984, he completed his Ph.D. degree in Materials Science and Engineering, also at the University of Illinois, with Samuel Stupp (1989). He then went to the California Institute of Technology as an NSF postdoctoral fellow to study with Robert Grubbs. In 1990 he joined the chemistry faculty at the University of Michigan in Ann Arbor. He returned to the University of Illinois in 1993, where he is currently a Professor of Chemistry and Materials Science and Engineering. In 1995 he became a part-time faculty member of the Beckman Institute for Advanced Science and Technology, where he now serves as co-chairman of the Molecular and Electronic Nanostructures Main Research Theme. Ryan B. Prince was born in Robbinsdale, MN, in 1972. He graduated from Southeast Missouri State University in 1995 with his B.S. degree in Chemistry, where he worked for Professor Jin K. Gong on the synthesis and characterization of transition-metal complexes that bind and activate carbon dioxide. He then went to the University of Illinois and worked with Professor Jeffrey...

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Section: The γ-Peptide Family1 γ-Peptide Foldamersmentioning

confidence: 99%

Section: γ-Peptide Foldamersmentioning

confidence: 99%

A Field Guide to Foldamers

et al. 2001

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“…The g-dipeptide 45 does not have the same topology as a b-II-hairpin 3 or as 4; it has two atoms less in the turn. Otherwise the side arms in 45 are conformationally pre-organized [31] in a similar manner as in the hairpin mimetic 4 described above. Whereas, in 4, a lack of conformational pre-organization about the bonds C(1)ÀC(2) and C(11)ÀN(12) turned out to be the Achilles heel of the overall design, it is these two bonds that are missing in 45.…”

Section: Scheme 1 Schemementioning

confidence: 88%

Synthesis of a Conformationally Flexible β‐Hairpin Mimetic

Hoffmann

Schopfer

Müller³

et al. 2002

Helvetica Chimica Acta

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Dedicated to Professor Dieter Seebach on the occasion of his 65th birthday Rational conformation design led us to a synthesis of the w-amido-undecenamide 4, which was shown by theoretical means (simulated annealing techniques) and by NMR and IR spectroscopy to have a high tendency to populate a conformation corresponding to a natural b-II'-type hairpin, despite possessing a conformationally fully flexible open-chain backbone.

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“…† The procedure for the preparation of 12c, and the characterisation data, have been reported. 25 J Values are given in Hz and optical rotations in 10 Ϫ1 deg cm 2 g Ϫ1 .…”

Section: Methodsmentioning

confidence: 99%