Organic Letters 1999-12-02

Non-hydrogen-bonded secondary structure in beta-peptides: evidence from circular dichroism of (S)-pyrrolidine-3-carboxylic acid oligomers and (S)-nipecotic acid oligomers.

B R Huck, J M Langenhan, S H Gellman

Index: Org. Lett. 1(11) , 1717-20, (1999)

Full Text: HTML

Abstract

[formula: see text] Homooligomers of beta-amino acids (S)-3-pyrrolidine-3-carboxylic acid (PCA) and (S)-nipecotic acid (Nip) were studied by circular dichroism (CD) in methanol. In each series, a profound change in the far-UV CD spectrum was observed from monomer to tetramer, but little change was observed from tetramer to hexamer. A comparable pattern is observed in the CD spectra of short proline oligomers. We conclude that both PCA and Nip oligomers with > or = four residues adopt a characteristic secondary structure.


Related Compounds

Related Articles:

Diastereocontrolled synthesis of enantioenriched 3,4-disubstituted beta-prolines.

2007-01-19

[J. Org. Chem. 72 , 398, (2007)]

Beta-proline analogues as agonists at the strychnine-sensitive glycine receptor.

1992-01-24

[J. Med. Chem. 35 , 233, (1992)]

Endomorphin-1 analogues containing beta-proline are mu-opioid receptor agonists and display enhanced enzymatic hydrolysis resistance.

2002-06-06

[J. Med. Chem. 45(12) , 2571-8, (2002)]

Catalysis of 3-pyrrolidinecarboxylic acid and related pyrrolidine derivatives in enantioselective anti-Mannich-type reactions: importance of the 3-acid group on pyrrolidine for stereocontrol.

2008-01-23

[J. Am. Chem. Soc. 130(3) , 875-86, (2008)]

Constrained beta-proline analogues in organocatalytic aldol reactions: the influence of acid geometry.

2009-07-17

[J. Org. Chem. 74(14) , 5041-8, (2009)]

More Articles...