Volume 4, Issue 1, Pages 124-137 (January 2018) Light Harvesting for Rapid and Selective Reactions: Click Chemistry with Strain- Loadable Alkenes Kamaljeet Singh, Christopher J. Fennell, Evangelos A. Coutsias, Reza Latifi, Steve Hartson, Jimmie D. Weaver Chem Volume 4, Issue 1, Pages 124-137 (January 2018) DOI: 10.1016/j.chempr.2017.11.007 Copyright © 2017 Elsevier Inc. Terms and Conditions
Chem 2018 4, 124-137DOI: (10.1016/j.chempr.2017.11.007) Copyright © 2017 Elsevier Inc. Terms and Conditions
Figure 1 Conjugation Strategies Chem 2018 4, 124-137DOI: (10.1016/j.chempr.2017.11.007) Copyright © 2017 Elsevier Inc. Terms and Conditions
Figure 2 Demonstration of Biotin Conjugation to Insulin via Strain-Loadable Alkene Coupling There are three modifiable sites on the insulin structure highlighted in red: the N termini on the A and B strands and the lysine residue on the B strand. The matrix-assisted laser desorption/ionization spectra on the right show modification and identification of two variants of the monoconjugated protein. Chem 2018 4, 124-137DOI: (10.1016/j.chempr.2017.11.007) Copyright © 2017 Elsevier Inc. Terms and Conditions
Scheme 1 The Development of the Molecular Mousetrap (A) First effort to capture photochemical energy as ring strain. (B) Attempts to chemically capture strained alkenes. Significant dimerization was observed for entries 3 and 4; see Supplemental Information for details. (C) Calculated torsion angle energy landscapes about the ring alkene bonds in (left) PC7 and (right) BC7. (D) Reaction results for BC6, BC7, and BC8 triazoline formation. (E) Two views of the crystal structure of the major product, showing the trans-ring fusion. Chem 2018 4, 124-137DOI: (10.1016/j.chempr.2017.11.007) Copyright © 2017 Elsevier Inc. Terms and Conditions
Scheme 2 Visible-Light-Mediated [3 + 2] Cycloaddition of Benzofused Cycloheptenes and Azides Chem 2018 4, 124-137DOI: (10.1016/j.chempr.2017.11.007) Copyright © 2017 Elsevier Inc. Terms and Conditions
Scheme 3 Reaction Outcome in the Presence of Various Fluorophores Chem 2018 4, 124-137DOI: (10.1016/j.chempr.2017.11.007) Copyright © 2017 Elsevier Inc. Terms and Conditions