Fully automated synthesis of 13N-labeled nitrosothiols

Tetrahedron Letters

Volumn 51, Issue 22, 2010, Pages 2990-2993

  Gómez Vallejo, Vanessa ^a   Kato, Koichi ^b   Oliden, Iosu ^a   Calvo, Javier ^a   Baz, Zuriñe ^a   Borrell, José I ^c   Llop, Jordi ^a  

^a CIC BIOMAGUNE   (Spain)

^b NATIONAL INSTITUTE OF RADIOLOGICAL SCIENCES   (Japan)

^c INSTITUT QUÍMIC DE SARRIÀ   (Spain)

Author keywords

Nitrogen 13; Nitrosothiols; Positron emission tomography

Indexed keywords

ANION EXCHANGE RESIN; NITROGEN 13; NITROGEN DIOXIDE; S NITROSOTHIOL; THIOL DERIVATIVE; TRACER;

ARTICLE; CHEMICAL STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; PURIFICATION; RADIOCHEMISTRY; SOLID PHASE EXTRACTION; SYNTHESIS;

EID: 77951620632     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.03.122     Document Type: Article

References (18)

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9. The scheme of the automated system, the characteristics of the individual components and details about synthetic steps are included as Supplementary data.
10. 4Cl solution (2 × 20 mL), and distilled water (3 × 20 mL). The column showed excellent reductive properties for up to 10 consecutive runs within one day. Reconditioning on a daily basis ensured optimal performance for up to 100 runs.
11. 13N]nitrosothiols 1-5 were purchased from Sigma-Aldrich and used without further purification. For the synthesis of 2-(N-acetyl-d-penicillamido)-2-deoxy-1,3,4,6-tetra-O-acetyl-β-d-glu copyranose (precursor for 6), the methodology described in Ref. 12 was followed.
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13. For analytical HPLC, an Agilent 1200 Series HPLC system with a multiple wavelength detector (λ = 220 nm) and a radiometric detector was used. A Mediterranean SeaRP-18 column (5 μm, 150 mm, 4.6 mm) was used as stationary phase. For compounds 1-4 and 6, water/methanol/acetonitrile (10:15:75) was used as mobile phase at a flow rate of 1 mL/min. For compound 5, aqueous TFA solution/acetonitrile (95:5) was used at a flow rate of 1 mL/min.
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15. For semi-preparative HPLC, an isocratic pump (Knauer) with a radiometric detector was used. A Mediterranean Sea18 column (5 μm, 250 mm, 10 mm) was used as stationary phase. For compounds 1-4 and 6, water/ethanol/acetonitrile (10:15:75) was used as mobile phase at a flow rate of 6 mL/min. For compound 5, aqueous TFA solution/ethanol (85:15) was used at a flow rate of 4 mL/min.
16. UPLC/MS analyses were performed using an AQUITY UPLC separation module coupled to a LCT TOF Premier XE mass spectrometer (Waters, Manchester, UK). An Acquity BEH C18 column (1.7 μm, 5 mm, 2.1 mm) was used as stationary phase. The elution buffers were A (methanol and 0.1% formic acid) and B (water and 0.1% formic acid). The column was eluted with a linear gradient consisted of 95% A to 1% over 2.5 min, 1% over 2.5-3.5 min, returned to 95 for 0.5 min and kept for a further 1 min. Total run was 5 min, injection volume was 5 μL and the flow rate 600 μL/min. Detection was performed in positive ion mode in the range of 50-1000, with a scan time of 1 s and a delay time of 0.1 s in centered mode. GSNO was detected as protonated molecule (m/z = 377.08, retention time = 0.81 min) and RIG was detected as sodium adduct (m/z = 572.15, retention time = 1.78 min).
17. Scenario 1: as reported in Ref. 13; scenario 2: as reported in Ref. 16.
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