1,3-Dipolar cycloaddition of azides with electron-deficient alkynes under mild condition in water

Tetrahedron Letters

Volumn 45, Issue 15, 2004, Pages 3143-3146

  Li, Zengmin ^a,b   Seo, Tae Seok ^a,b   Ju, Jingyue ^a,b  

^a College of Physicians and Surgeons ^*  (United States)

^b Columbia University ^*  (United States)

Author keywords

1,3 Dipolar cycloaddition; 5 Azido DNA; Electron deficient alkynes

Indexed keywords

ALKYNE; AZIDE; WATER;

ARTICLE; CATALYST; CYCLOADDITION; ELECTRON; EVALUATION; REACTION ANALYSIS; ROOM TEMPERATURE; SYNTHESIS;

EID: 1642281920     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.089     Document Type: Article

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24. +]; found, 368.1280. The crystallographic data of the entry 3 product has been deposited at the Cambridge Crystallographic Data Center with the deposition number CCDC 220803.
25. HPLC analysis: HPLC analysis was carried out on a Waters system consisting of a Rheodyne 7725I injector, a 600 Controller, Xterra MS C18 ( 4.6×50 -mm) column, and 996 photodiode array detector. Elution was performed by using a linear gradient (8-28%) of methanol in a buffer that consists of 8.6 mM aqueous triethylamine and 100 mM hexafluoroisopropyl alcohol (pH 8.1) at a flow rate of 0.5 mL/min with the temperature set at 50°C. Under this condition, the elution time of the entry 7 product was 49.6 min and that of the entry 8 product was 28.2 min. MALDI-TOF MS analysis: Mass measurement of oligonucleotides was performed using a Voyager™ DE MALDI-TOF mass spectrometer. DNA product (20 pmol) was suspended in 2 μL of 3-hydroxypicolinic acid matrix solution. This mixture (0.5 μL) was spotted on a stainless steel sample plate, air-dried, and analyzed. The measurement was taken using a positive ion mode with 25 kV accelerating voltage, 94% grid voltage and a 350 ns delay time with internal calibration.