β-Azidoalanine as an IR probe: Application to amyloid Aβ(16-22) aggregation

Kwang Im Oh, Joo Hyun Lee, Cheonik Joo, Hogyu Han, Minhaeng Cho

Research output: Contribution to journalArticle

82 Citations (Scopus)

Abstract

β-Azidoalanine dipeptide 1 was synthesized, and its azido stretching vibration in H2O and dimethyl sulfoxide (DMSO) was studied by using Fourier transform (FT) IR spectroscopy. The dipole strength of the azido stretch mode is found to be about 19 and 5 times larger than those of the CN and SCN stretch modes, respectively, which have been used as local environmental IR sensors. The azido stretch band in H2O is blue-shifted by about 14 cm-1 in comparison to that in DMSO, indicative of its sensitivity to the electrostatic environment. To test the utility of β-azidoalanine as an IR probe of the local electrostatic environment in proteins, azidopeptide 4 was prepared by its incorporation into Aβ(16-22) peptide of the Alzheimer's disease amyloid β-protein at position Ala21. The amide I IR spectrum of 4 in D2O suggests that the azidopeptide thus modified forms in-register β-sheets in aggregates as observed for normal Aβ(16-22). The azido peak frequency of 4 in aggregates is almost identical to that in DMSO, indicating that the azido group is not exposed to water but to the hydrophobic environment. We believe that β-azidoalanine will be used as an effective IR probe for providing site-specific information about the local electrostatic environments of proteins.

Original languageEnglish
Pages (from-to)10352-10357
Number of pages6
JournalJournal of Physical Chemistry B
Volume112
Issue number33
DOIs
Publication statusPublished - 2008 Aug 21

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Dimethyl sulfoxide
Dimethyl Sulfoxide
Amyloid
Electrostatics
Agglomeration
probes
electrostatics
proteins
Proteins
Amyloidogenic Proteins
Dipeptides
Amides
Peptides
Stretching
Infrared spectroscopy
Fourier transforms
registers
amides
peptides
Water

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry

Cite this

β-Azidoalanine as an IR probe : Application to amyloid Aβ(16-22) aggregation. / Oh, Kwang Im; Lee, Joo Hyun; Joo, Cheonik; Han, Hogyu; Cho, Minhaeng.

In: Journal of Physical Chemistry B, Vol. 112, No. 33, 21.08.2008, p. 10352-10357.

Research output: Contribution to journalArticle

Oh, Kwang Im ; Lee, Joo Hyun ; Joo, Cheonik ; Han, Hogyu ; Cho, Minhaeng. / β-Azidoalanine as an IR probe : Application to amyloid Aβ(16-22) aggregation. In: Journal of Physical Chemistry B. 2008 ; Vol. 112, No. 33. pp. 10352-10357.
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