Facile synthesis of stapled, structurally reinforced peptide helices via a photoinduced intramolecular 1,3-dipolar cycloaddition reaction

Michael M. Madden; Claudia I. Rivera Vera; Wenjiao Song; Qing Lin

doi:10.1039/b912094g

Facile synthesis of stapled, structurally reinforced peptide helices via a photoinduced intramolecular 1,3-dipolar cycloaddition reaction

Michael M. Madden
, Claudia I. Rivera Vera
, Wenjiao Song
, Qing Lin

Chemistry

SUNY Buffalo

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

72 Scopus citations

Abstract

We report the first use of a photoinduced 1,3-dipolar cycloaddition reaction in "stapling" peptide sidechains to reinforce a model peptide helical structure with moderate to excellent yields; the resulting pyrazoline "staplers" exhibit unique fluorescence useful in a cell permeability study.

Original language	English
Pages (from-to)	5588-5590
Number of pages	3
Journal	Chemical Communications
Issue number	37
DOIs	https://doi.org/10.1039/b912094g
State	Published - 2009

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title = "Facile synthesis of stapled, structurally reinforced peptide helices via a photoinduced intramolecular 1,3-dipolar cycloaddition reaction",

abstract = "We report the first use of a photoinduced 1,3-dipolar cycloaddition reaction in {"}stapling{"} peptide sidechains to reinforce a model peptide helical structure with moderate to excellent yields; the resulting pyrazoline {"}staplers{"} exhibit unique fluorescence useful in a cell permeability study.",

author = "Madden, \{Michael M.\} and \{Rivera Vera\}, \{Claudia I.\} and Wenjiao Song and Qing Lin",

year = "2009",

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journal = "Chemical Communications",

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T1 - Facile synthesis of stapled, structurally reinforced peptide helices via a photoinduced intramolecular 1,3-dipolar cycloaddition reaction

AU - Madden, Michael M.

AU - Rivera Vera, Claudia I.

AU - Song, Wenjiao

AU - Lin, Qing

PY - 2009

Y1 - 2009

N2 - We report the first use of a photoinduced 1,3-dipolar cycloaddition reaction in "stapling" peptide sidechains to reinforce a model peptide helical structure with moderate to excellent yields; the resulting pyrazoline "staplers" exhibit unique fluorescence useful in a cell permeability study.

AB - We report the first use of a photoinduced 1,3-dipolar cycloaddition reaction in "stapling" peptide sidechains to reinforce a model peptide helical structure with moderate to excellent yields; the resulting pyrazoline "staplers" exhibit unique fluorescence useful in a cell permeability study.

UR - https://www.scopus.com/pages/publications/70349267662

U2 - 10.1039/b912094g

DO - 10.1039/b912094g

M3 - Article

C2 - 19753366

AN - SCOPUS:70349267662

SN - 1359-7345

SP - 5588

EP - 5590

JO - Chemical Communications

JF - Chemical Communications

IS - 37

ER -

Facile synthesis of stapled, structurally reinforced peptide helices via a photoinduced intramolecular 1,3-dipolar cycloaddition reaction

Abstract

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