Secondary structural preferences of 2,2-disubstituted pyrrolidine-4-carboxylic acid oligomers: beta-peptide foldamers that cannot form internal hydrogen bonds.

Secondary structural preferences of 2,2-disubstituted pyrrolidine-4-carboxylic acid oligomers: beta-peptide foldamers that cannot form internal hydrogen bonds. Research Abstract Details 

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Secondary structural preferences of 2,2-disubstituted pyrrolidine-4-carboxylic acid oligomers: beta-peptide foldamers that cannot form internal hydrogen bonds. Abstract Text:

Bayard R Huck,John D Fisk,Ilia A Guzei,Heather A Carlson,Samuel H Gellman,

We examine a new class of beta-peptides, 2,2-disubstituted pyrrolidine-4-carboxylic acid oligomers, and show that they manifest discrete conformational preferences despite the impossibility of internal hydrogen bonding. Numerous beta-peptide families have been described that display specific secondary structural preferences, but all of the conformations characterized in detail so far have contained internal hydrogen bonds. Internal hydrogen bonding is observed within the most common secondary structures of conventional peptides as well. Identifying foldamers in which shape control is independent of hydrogen bonding is significant in two ways. At a fundamental level, foldamers in this small but growing class are interesting because their shapes are controlled by distinctive networks of noncovalent forces. At a practical level, non-hydrogen bonded foldamers may be useful in biomedical applications because the low intrinsic polarity of their backbones may promote bioavailability.

Secondary structural preferences of 2,2-disubstituted pyrrolidine-4-carboxylic acid oligomers: beta-peptide foldamers that cannot form internal hydrogen bonds. Publishing Authors By Initials

BR Huck,JD Fisk,IA Guzei,HA Carlson,SH Gellman,

For similar heterocyclic compounds: heterocyclic compounds, 1-ring: pyrrolidines research abstracts see: heterocyclic compounds: heterocyclic compounds, 1-ring: pyrrolidines research

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Secondary structural preferences of 2,2-disubstituted pyrrolidine-4-carboxylic acid oligomers: beta-peptide foldamers that cannot form internal hydrogen bonds. Journal Published:

PUBLICATION TYPE: Research Support, U.S. Gov't,

Journal: Journal of the American Chemical Society

VOLUME: 125

Page Numbers: 9035-7

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 0002-7863

DAY: 30

MONTH: Jul

YEAR: 2003

Secondary structural preferences of 2,2-disubstituted pyrrolidine-4-carboxylic acid oligomers: beta-peptide foldamers that cannot form internal hydrogen bonds. Information

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LANGUAGE: eng

NlmUniqueID: 7503056

Secondary structural preferences of 2,2-disubstituted pyrrolidine-4-carboxylic acid oligomers: beta-peptide foldamers that cannot form internal hydrogen bonds. Keywords Mesh Terms:

KEYWORDS: Pyrrolidines

MESH TERMS: chemistry

Chemical & Substance for Abstract: Secondary structural preferences of 2,2-disubstituted pyrrolidine-4-carboxylic acid oligomers: beta-peptide foldamers that cannot form internal hydrogen bonds. Information

Substance Name: Pyrrolidines

Registry Number: 0

Grant and Affiliation Information for Secondary structural preferences of 2,2-disubstituted pyrrolidine-4-carboxylic acid oligomers: beta-peptide foldamers that cannot form internal hydrogen bonds.

AFFILIATION: Department of Chemistry and Graduate Program in Biophysics, University of Wisconsin, Madison, WI 53706, USA.

Country: United States

AGENCY: United States NIGMS

GRANT: GM 65372

ACRONYM: GM

MEDLINETA: J Am Chem Soc

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