Peptide bond mimicry by (E)-alkene and (Z)-fluoroalkene peptide isosteres: Synthesis and bioevaluation of α-helical anti-HIV peptide analogues

Shinya Oishi; Hirotaka Kamitani; Yasuyo Kodera; Kentaro Watanabe; Kazuya Kobayashi; Tetsuo Narumi; Kenji Tomita; Hiroaki Ohno; Takeshi Naito; Eiichi Kodama; Masao Matsuoka; Nobutaka Fujii

doi:10.1039/b907983a

Peptide bond mimicry by (E)-alkene and (Z)-fluoroalkene peptide isosteres: Synthesis and bioevaluation of α-helical anti-HIV peptide analogues

Shinya Oishi, Hirotaka Kamitani, Yasuyo Kodera, Kentaro Watanabe, Kazuya Kobayashi, Tetsuo Narumi, Kenji Tomita, Hiroaki Ohno, Takeshi Naito, Eiichi Kodama, Masao Matsuoka, Nobutaka Fujii

IRIDeS - Disaster Medical Science Division

Kyoto University

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

102 Citations (Scopus)

Abstract

The α-helix structures of the anti-HIV fusion inhibitory peptides are stabilized by the amino acid sequence and by intrachain hydrogen bonds. The study of peptide analogues using (E)-alkene and (Z)-fluoroalkene dipeptide isosteres demonstrated the substantial, yet position-dependent, contribution of hydrogen bonds to the α-helix stability and anti-HIV bioactivity.

Original language	English
Pages (from-to)	2872-2877
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	7
Issue number	14
DOIs	https://doi.org/10.1039/b907983a
Publication status	Published - 2009

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10.1039/b907983a

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Oishi, S., Kamitani, H., Kodera, Y., Watanabe, K., Kobayashi, K., Narumi, T., Tomita, K., Ohno, H., Naito, T., Kodama, E., Matsuoka, M., & Fujii, N. (2009). Peptide bond mimicry by (E)-alkene and (Z)-fluoroalkene peptide isosteres: Synthesis and bioevaluation of α-helical anti-HIV peptide analogues. Organic and Biomolecular Chemistry, 7(14), 2872-2877. https://doi.org/10.1039/b907983a

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abstract = "The α-helix structures of the anti-HIV fusion inhibitory peptides are stabilized by the amino acid sequence and by intrachain hydrogen bonds. The study of peptide analogues using (E)-alkene and (Z)-fluoroalkene dipeptide isosteres demonstrated the substantial, yet position-dependent, contribution of hydrogen bonds to the α-helix stability and anti-HIV bioactivity.",

author = "Shinya Oishi and Hirotaka Kamitani and Yasuyo Kodera and Kentaro Watanabe and Kazuya Kobayashi and Tetsuo Narumi and Kenji Tomita and Hiroaki Ohno and Takeshi Naito and Eiichi Kodama and Masao Matsuoka and Nobutaka Fujii",

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Oishi, S, Kamitani, H, Kodera, Y, Watanabe, K, Kobayashi, K, Narumi, T, Tomita, K, Ohno, H, Naito, T, Kodama, E, Matsuoka, M & Fujii, N 2009, 'Peptide bond mimicry by (E)-alkene and (Z)-fluoroalkene peptide isosteres: Synthesis and bioevaluation of α-helical anti-HIV peptide analogues', Organic and Biomolecular Chemistry, vol. 7, no. 14, pp. 2872-2877. https://doi.org/10.1039/b907983a

TY - JOUR

T1 - Peptide bond mimicry by (E)-alkene and (Z)-fluoroalkene peptide isosteres

T2 - Synthesis and bioevaluation of α-helical anti-HIV peptide analogues

AU - Oishi, Shinya

AU - Kamitani, Hirotaka

AU - Kodera, Yasuyo

AU - Watanabe, Kentaro

AU - Kobayashi, Kazuya

AU - Narumi, Tetsuo

AU - Tomita, Kenji

AU - Ohno, Hiroaki

AU - Naito, Takeshi

AU - Kodama, Eiichi

AU - Matsuoka, Masao

AU - Fujii, Nobutaka

PY - 2009

Y1 - 2009

N2 - The α-helix structures of the anti-HIV fusion inhibitory peptides are stabilized by the amino acid sequence and by intrachain hydrogen bonds. The study of peptide analogues using (E)-alkene and (Z)-fluoroalkene dipeptide isosteres demonstrated the substantial, yet position-dependent, contribution of hydrogen bonds to the α-helix stability and anti-HIV bioactivity.

AB - The α-helix structures of the anti-HIV fusion inhibitory peptides are stabilized by the amino acid sequence and by intrachain hydrogen bonds. The study of peptide analogues using (E)-alkene and (Z)-fluoroalkene dipeptide isosteres demonstrated the substantial, yet position-dependent, contribution of hydrogen bonds to the α-helix stability and anti-HIV bioactivity.

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DO - 10.1039/b907983a

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SP - 2872

EP - 2877

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 14

ER -

Peptide bond mimicry by (E)-alkene and (Z)-fluoroalkene peptide isosteres: Synthesis and bioevaluation of α-helical anti-HIV peptide analogues

Abstract

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