"@-Tides": The 1,2-dihydro-3(6h)-pyridinone unit as a β-strand mimic

S. T. Phillips; M. Rezac; U. Abel; M. Kossenjans; P. A. Bartlett

doi:10.1021/ja0168460

"@-Tides": The 1,2-dihydro-3(6h)-pyridinone unit as a β-strand mimic

S. T. Phillips
, M. Rezac
, U. Abel
, M. Kossenjans
, P. A. Bartlett

Micron School of Materials Science and Engineering

University of California at Berkeley

Research output: Contribution to journal › Article › peer-review

74 Scopus citations

Abstract

The cyclic amino acid surrogate 1 was designed to mimic the extended conformation of a peptide unit and to provide hydrogen bond donor and acceptor functions conducive to β-sheet formation. A convenient synthesis of this unit and solution and solid-phase methods for its incorporation into an oligomer alternating with peptide units have been devised. The resulting "@-tides", as these oligomers have been designated, show a high propensity for self-association in comparison to oligopeptides; insights into the structure and dynamical properties of their antiparallel dimers have been obtained by NMR.

Original language	English
Pages (from-to)	58-66
Number of pages	9
Journal	Journal of the American Chemical Society
Volume	124
Issue number	1
DOIs	https://doi.org/10.1021/ja0168460
State	Published - 9 Jan 2002

Keywords

Kinetics
Molecular Mimicry
Nuclear Magnetic Resonance, Biomolecular
Oligopeptides/chemistry
Protein Structure, Secondary
Pyridones/chemical synthesis
Temperature

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10.1021/ja0168460

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abstract = "The cyclic amino acid surrogate 1 was designed to mimic the extended conformation of a peptide unit and to provide hydrogen bond donor and acceptor functions conducive to β-sheet formation. A convenient synthesis of this unit and solution and solid-phase methods for its incorporation into an oligomer alternating with peptide units have been devised. The resulting {"}@-tides{"}, as these oligomers have been designated, show a high propensity for self-association in comparison to oligopeptides; insights into the structure and dynamical properties of their antiparallel dimers have been obtained by NMR.",

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year = "2002",

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T2 - The 1,2-dihydro-3(6h)-pyridinone unit as a β-strand mimic

AU - Phillips, S. T.

AU - Rezac, M.

AU - Abel, U.

AU - Kossenjans, M.

AU - Bartlett, P. A.

PY - 2002/1/9

Y1 - 2002/1/9

N2 - The cyclic amino acid surrogate 1 was designed to mimic the extended conformation of a peptide unit and to provide hydrogen bond donor and acceptor functions conducive to β-sheet formation. A convenient synthesis of this unit and solution and solid-phase methods for its incorporation into an oligomer alternating with peptide units have been devised. The resulting "@-tides", as these oligomers have been designated, show a high propensity for self-association in comparison to oligopeptides; insights into the structure and dynamical properties of their antiparallel dimers have been obtained by NMR.

AB - The cyclic amino acid surrogate 1 was designed to mimic the extended conformation of a peptide unit and to provide hydrogen bond donor and acceptor functions conducive to β-sheet formation. A convenient synthesis of this unit and solution and solid-phase methods for its incorporation into an oligomer alternating with peptide units have been devised. The resulting "@-tides", as these oligomers have been designated, show a high propensity for self-association in comparison to oligopeptides; insights into the structure and dynamical properties of their antiparallel dimers have been obtained by NMR.

KW - Kinetics

KW - Molecular Mimicry

KW - Nuclear Magnetic Resonance, Biomolecular

KW - Oligopeptides/chemistry

KW - Protein Structure, Secondary

KW - Pyridones/chemical synthesis

KW - Temperature

UR - https://www.scopus.com/pages/publications/0037045238

U2 - 10.1021/ja0168460

DO - 10.1021/ja0168460

M3 - Article

C2 - 11772062

AN - SCOPUS:0037045238

SN - 0002-7863

VL - 124

SP - 58

EP - 66

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 1

ER -

"@-Tides": The 1,2-dihydro-3(6h)-pyridinone unit as a β-strand mimic

Abstract

Keywords

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