Synthesis of 4,4-disubstituted 2-aminocyclopentanecarboxylic acid derivatives and their incorporation into 12-helical β-peptides

Organic Letters

Volumn 6, Issue 24, 2004, Pages 4411-4414

  Peelen, Timothy J ^a   Chi, Yonggui ^a   English, Emily Payne ^a   Gellman, Samuel H ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOCYCLOPENTANECARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; CYCLOPENTANE DERIVATIVE; PEPTIDE DERIVATIVE;

ACIDITY; AQUEOUS SOLUTION; ARTICLE; DRUG CONFORMATION; DRUG DESIGN; DRUG SYNTHESIS; ENANTIOSELECTIVITY; GEOMETRY; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUBSTITUTION REACTION; TRANS ISOMER;

CARBOXYLIC ACIDS; MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDES; PROTEIN STRUCTURE, SECONDARY; STEREOISOMERISM;

EID: 10044287252     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0483293     Document Type: Article

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31. S)-α-Methylbenzylamine was used with β-ketoesters 11c and 11d, not the (R)-enantiomer as shown.
32. Compound 12c was purified from the other diastereomeric products by selective recrystallization of the amine 12c·HCl salt, not column chromatography.
33. See Supporting Information.
34. The stereochemistry of 12d and 13d could be determined by incorporating 14d and ent-14d into short β-peptides containing cyclic β-amino acid residues with known configuration, including (S,S)-ACPC. The matched β-peptide, containing 14d, showed a 12-helical signature by CD, whereas the mismatched β-peptide, containing ent-14d, showed a very different CD signature.
35. ent-14c could be incorporated into β-peptides and deprotected with no observed decarboxylation of the β-dicarboxylic acids; see Supporting Information.
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38. Hα(i + 3) NOEs will be examined with larger β-peptides in the future.