Phenylisoserine: A Versatile Amino Acid for the Construction of Novel β-Peptide Structures

doi:10.1021/JA002700+

Paper

Phenylisoserine: A Versatile Amino Acid for the Construction of Novel β-Peptide Structures

Published Jan 10, 2001 · I. Motorina, C. Huel, E. Quiniou

Journal of the American Chemical Society

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21

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0

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Abstract

The N-Boc O-tert-butyldimethysilyl-substituted hexa-β-peptide methyl ester 18 was constructed from the O-TBS ether of (−)-(2R, 3S)-phenylisoserine. By NMR, it was determined that this homo β-peptide adopts a highly stable β-strand-type secondary structure in chloroform solution, which is stabilized by both hydrophobic interactions involving the OTBS methyl groups of residues i and i + 2, and inter-(five-membered)/intra (six-membered)-residue H-bonding interactions. These interactions are systematically repeated along the peptide chain and, thereby, operate in concert to stabilize the observed conformation of 18.

Study Snapshot

Phenylisoserine is a versatile amino acid for the construction of novel -peptide structures, with its stability attributed to hydrophobic interactions and inter-residue H-bonding interactions.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Phenylisoserine: A Versatile Amino Acid for the Construction of Novel β-Peptide Structures

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