Chemoselective Formation of Successive Triazole Linkages in One Pot: “Click−Click” Chemistry Export

@article{citeulike:5850035, abstract = {PMID: 16986936 A methodology for the successive regiospecific clicking together of three components in one pot via two triazole linkages is reported. The protocol utilizes copper(I)-mediated alkyneazide cycloaddition reactions combined with a silver(I)-catalyzed TMS-alkyne deprotection under mild hydroalcoholic conditions. We exemplify the approach with peptide-based components to illustrate its compatibility with polyfunctionalized biomolecules. The method constitutes a promising tool for peptide ligation. We also provide a procedure for directly using TMS-alkynes as the cycloaddition partner in classical click chemistry.}, author = {Aucagne, Vincent and Leigh, David A.}, citeulike-article-id = {5850035}, citeulike-linkout-0 = {http://dx.doi.org/10.1021/ol061657d}, citeulike-linkout-1 = {http://pubs.acs.org/doi/abs/10.1021/ol061657d}, day = {1}, doi = {10.1021/ol061657d}, journal = {Organic Letters}, keywords = {aucagne, click, leigh, ligation, methodology}, month = {September}, number = {20}, pages = {4505--4507}, posted-at = {2009-09-29 16:17:50}, priority = {2}, title = {Chemoselective Formation of Successive Triazole Linkages in One Pot: ” Click−Click” Chemistry}, url = {http://dx.doi.org/10.1021/ol061657d}, volume = {8}, year = {2006} }

TY - JOUR ID - citeulike:5850035 L3 - citeulike-article-id:5850035 N2 - PMID: 16986936 A methodology for the successive regiospecific clicking together of three components in one pot via two triazole linkages is reported. The protocol utilizes copper(I)-mediated alkyneazide cycloaddition reactions combined with a silver(I)-catalyzed TMS-alkyne deprotection under mild hydroalcoholic conditions. We exemplify the approach with peptide-based components to illustrate its compatibility with polyfunctionalized biomolecules. The method constitutes a promising tool for peptide ligation. We also provide a procedure for directly using TMS-alkynes as the cycloaddition partner in classical click chemistry. IS - 20 JF - Organic Letters EP - 4507 TI - Chemoselective Formation of Successive Triazole Linkages in One Pot: “Click−Click” Chemistry VL - 8 SP - 4505 KW - aucagne KW - click KW - leigh KW - ligation KW - methodology AU - Aucagne, Vincent AU - Leigh, David PY - 2006/09/01/ UR - http://dx.doi.org/10.1021/ol061657d ER -