Synthesis of a Dual-Labeled Probe of Dimethyl Lithospermate B with Photochemical and Fluorescent Properties
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of DLB Photoaffinity Probe
2.2. Photochemical and Fluorescent Evaluation
3. Experimental
3.1. General
3.2. (2S,3S)-(R)-3-(2,2-Diphenylbenzo[d][1,3]dioxol-5-yl)-1-methoxy-1-oxopropan-2-yl)2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-4-((E)-3-((R)-3-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-1-methoxy-1-oxopropan-2-yloxy)-3-oxoprop-1-enyl)-7-hydroxy-2,3-dihydrobenzofuran-3-carboxylate (4)
3.3. (2S,3S)-(R)-3-(2,2-Diphenylbenzo[d][1,3]dioxol-5-yl)-1-methoxy-1-oxopropan-2-yl) 2-(2,2-diphenyl benzo[d][1,3]dioxol-5-yl)-4-(E)-3-(R)-3-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-1-methoxy-1-oxopropan-2-yloxy)-3-oxoprop-1-enyl)-7-(4-nitrophenoxy)carbonyloxy)-2,3-dihydrobenzofuran-3-carboxylate (5)
3.4. (2S,3S)-(R)-3-(2,2-Diphenylbenzo[d][1,3]dioxol-5-yl)-1-methoxy-1-oxopropan-2-yl) 7-(2,2-dimethyl-4-oxo-3,9,12,15-tetraoxa-5-azaoctadecan-18-ylcarbamoyloxy)-2-(2,2-diphenylbenzo [d] [1,3]dioxol-5-yl)-4-(E)-3-((R)-3-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-1-methoxy-1-oxopropan-2-yloxy)-3-oxoprop-1-enyl)-2,3-dihydrobenzofuran-3-carboxylate (7)
3.5. (R)-Methyl-6-(tert-butoxycarbonylamino)-2-(5-(dimethylamino)naphthalene-1-sulfonamido)hexanoate (13)
3.6. (R)-Methyl-2-(5-(dimethylamino)naphthalene-1-sulfonamido)-6-(2-methoxy-4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzamido)hexanoate (14)
3.7. (R)-2-(5-(Dimethylamino)naphthalene-1-sulfonamido)-6-(2-methoxy-4-(3-(trifluoromethyl)-3H-diazirin-3-yl)benzamido)hexanoic acid (15)
3.8. (2S,3S)-(R)-3-(3,4-Dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl) 2-(3,4-dihydroxyphenyl)-4-(E)-3-((R)-3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yloxy)-3-oxoprop-1-enyl)-7-(R)-7-(5-(dimethylamino)naphthalene-1-sulfonamido)-1-(2-methoxy-4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenyl)-1,8-dioxo-13,16,19-trioxa-2,9-diazadocosan-22-ylcarbamoyloxy)-2,3-dihydrobenzofuran-3-carboxylate (3)
3.9. (2S,3S)-((R)-3-(3,4-Dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yl) 2-(3,4-dihydroxyphenyl)-4-((E)-3-((R)-3-(3,4-dihydroxyphenyl)-1-methoxy-1-oxopropan-2-yloxy)-3-oxoprop-1-enyl)-7-((7R)-7-(5-(dimethylamino)naphthalene-1-sulfonamido)-1-(2-methoxy-4-(2,2,2-trifluoro-1-methoxyethyl)phenyl)-1,8-dioxo-13,16,19-trioxa-2,9-diazadocosan-22-ylcarbamoyloxy)-2,3-dihydrobenzofuran-3-carboxylate (16)
4. Conclusions
Supplementary Materials
Acknowledgements
References and Notes
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- Sample Availability: Samples of the compounds in mg scales are available from the authors.
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Lim, E.; Ricci, J.; Jung, M. Synthesis of a Dual-Labeled Probe of Dimethyl Lithospermate B with Photochemical and Fluorescent Properties. Molecules 2011, 16, 9886-9899. https://doi.org/10.3390/molecules16129886
Lim E, Ricci J, Jung M. Synthesis of a Dual-Labeled Probe of Dimethyl Lithospermate B with Photochemical and Fluorescent Properties. Molecules. 2011; 16(12):9886-9899. https://doi.org/10.3390/molecules16129886
Chicago/Turabian StyleLim, Eunyoung, Jeremy Ricci, and Mankil Jung. 2011. "Synthesis of a Dual-Labeled Probe of Dimethyl Lithospermate B with Photochemical and Fluorescent Properties" Molecules 16, no. 12: 9886-9899. https://doi.org/10.3390/molecules16129886