43:, carboxylic acid or a phosphate esters. For these groups stabilization systems have been developed depending on the protected part of a molecule: for a phosphate centre it is the "click-clack" approach, and for a hydroxyl group â the "chemical switch" concept.
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Brzezinska, J.; Witkowska, A.; BaĹabaĹska, S.; Chmielewski, M.K. â2-Pyridinyl-N-(2,4-difluorobenzyl)aminoethyl Group As
Thermocontrolled Implement for Protection of Carboxylic Acidsâ Organic Letters 18, 3230â3233 (2016) DOI: 10.1021/acs.orglett.6b01475
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depending either on nucleophilicity or configuration. TPGs are characterized by a different half-life after increasing temperature by 70 °C. The shortest deprotection time with high stability in lower temperatures has been found for
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Grajkowski A.; CieĹlak J., Chmielewski M.K., MarchĂĄn V., Phillips, L. R., and
Beaucage, S. L., Wilk A.; âConceptual âHeat-Drivenâ approach to the synthesis of DNA oligonucleotides on microarraysâ Ann. N.Y. Acad. Sci., 1002, 1-11
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Chmielewski M.K., MarchĂĄn V., CieĹlak J., Grajkowski A., Livengood V., MĂźchen U., Wilk A., Beaucage S.L., âThermolytic carbonates for potential 5â-hydroxyl protection of deoxyribonucleosidesâ J. Org. Chem., 68, 10003-10012
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Witkowska A., Krygier D., Brzezinska J., Chmielewski, M.K. âModulating the
Stability of 2-Pyridinyl Thermolabile Hydroxyl Protecting Groups via the âChemical Switchâ Approachâ J. Org. Chem., 80, 12129â12136 (2015)
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conditions are required. Their removal merely consists of increasing temperature, which leads to deprotection of the protected sensitive part of a molecule.
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Chmielewski M.K., âProtecting of a thermolabile protecting group: âClick-clackâ approachâ Organic
Letters, 11 (16) 3742-3745 (2009) DOI: 10.1021/ol901358d
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The deprotection mechanism has been proven only for several
Thermolabile Protecting Groups (TPGs). Most of these groups are removed on the basis of
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Chmielewski, Marcin K. (2012). "Novel thermolabile protecting groups with higher stability at ambient temperature".
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TPGs are applied as an element that increases the specificity of starters in
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39:TPGs that are applied to protect a
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17:Thermolabile Protecting Groups
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85:10.1016/j.tetlet.2011.11.122
135:DOI:10.1021/acs.joc.5b02033
50:; they may also be used in
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32:intramolecular cyclization
19:(TPGs) are applied in
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162:Chemical synthesis
21:chemical synthesis
167:Protecting groups
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79:(6): 666â669.
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