콘텐츠로 건너뛰기
Merck
  • A fluorogenic probe for the catalyst-free detection of azide-tagged molecules.

A fluorogenic probe for the catalyst-free detection of azide-tagged molecules.

Journal of the American Chemical Society (2012-10-26)
Frédéric Friscourt, Christoph J Fahrni, Geert-Jan Boons
초록

Fluorogenic reactions in which non- or weakly fluorescent reagents produce highly fluorescent products can be exploited to detect a broad range of compounds including biomolecules and materials. We describe a modified dibenzocyclooctyne that under catalyst-free conditions undergoes fast strain-promoted cycloadditions with azides to yield strongly fluorescent triazoles. The cycloaddition products are more than 1000-fold brighter compared to the starting cyclooctyne, exhibit large Stokes shift, and can be excited above 350 nm, which is required for many applications. Quantum mechanical calculations indicate that the fluorescence increase upon triazole formation is due to large differences in oscillator strengths of the S(0) ↔ S(1) transitions in the planar C(2v)-symmetric starting material compared to the symmetry-broken and nonplanar cycloaddition products. The new fluorogenic probe was successfully employed for labeling of proteins modified by an azide moiety.

MATERIALS
제품 번호
브랜드
제품 설명

Sigma-Aldrich
3-Ethynylanisole, 96%
로그인조직 및 계약 가격 보기
SKU팩 크기재고 정보가격수량
50 g
예상 입고일 January 31, 2025
세부사항...
₩799,211
100 g
예상 입고일 January 31, 2025
세부사항...
₩1,214,245
500 g
예상 입고일 January 31, 2025
세부사항...
₩4,473,105