Synthesis and Conformational Studies of gamma-Aminoxy Peptides.

Synthesis and Conformational Studies of gamma-Aminoxy Peptides. Research Abstract Details 

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Synthesis and Conformational Studies of gamma-Aminoxy Peptides. Abstract Text:

Fei Chen,Ke-Sheng Song,Yun-Dong Wu,Dan Yang,Fei Chen,Ke-Sheng Song,Yun-Dong Wu,Dan Yang,

We have synthesized a series of gamma-aminoxy acids, including unsubstituted and gamma4-Ph-, gamma4-alkyl-, and gamma3,4-cyclohexyl-substituted systems. Coupling of these monomers to oligomers can be realized using EDCI/HOBt (or HOAt) as the coupling agent. gamma-Aminoxy peptides can form 10-membered-ring intramolecular hydrogen bonds-so-called "gamma N-O turns"-between adjacent residues, the extent of which is controlled by the nature of the side chain of each gamma-aminoxy acid residue, increasing from the unsubstituted gamma-aminoxy peptide to the gamma4-alkyl aminoxy peptides to the gamma4-phenyl- and gamma3,4-cyclohexyl-substituted aminoxy peptides. The presence of two consecutive homochiral 10-membered-ring intramolecular hydrogen bonds leads to the formation of a novel helical structure. Theoretical studies on a series of model peptides rationalize very well the experimentally observed conformational features of these gamma-aminoxy peptides.

Synthesis and Conformational Studies of gamma-Aminoxy Peptides. Publishing Authors By Initials

F Chen,KS Song,YD Wu,D Yang,F Chen,KS Song,YD Wu,D Yang,

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Synthesis and Conformational Studies of gamma-Aminoxy Peptides. Journal Published:

PUBLICATION TYPE: Journal Article

Journal: Journal of the American Chemical Society

VOLUME: 130

Page Numbers: 743-55

Journal Abbreviation: J. Am. Chem. Soc.

ISSN: 1520-5126

DAY: 19

MONTH: 12

YEAR: 2007

Synthesis and Conformational Studies of gamma-Aminoxy Peptides. Information

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LANGUAGE: eng

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Grant and Affiliation Information for Synthesis and Conformational Studies of gamma-Aminoxy Peptides.

AFFILIATION: Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, People's Republic of China, and Department of Chemistry, Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong, People's Republic of China.

Country: United States

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MEDLINETA: J Am Chem Soc

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