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Your search keyword '"Maynard P"' showing total 16 results
Start Over Author "Maynard P" Journal journal of the american chemical society
16 results on '"Maynard P"'

1. Ultrafast Au(III)-Mediated Arylation of Cysteine

Author

Doud, Evan A, Tilden, James AR, Treacy, Joseph W, Chao, Elaine Y, Montgomery, Hayden R, Kunkel, Grace E, Olivares, Eileen J, Adhami, Nima, Kerr, Tyler A, Chen, Yu, Rheingold, Arnold L, Loo, Joseph A, Frost, Christopher G, Houk, KN, Maynard, Heather D, and Spokoyny, Alexander M

Subjects
Organic Chemistry, Chemical Sciences, Cysteine, Gold, Peptides, Organogold Compounds, Molecular Structure, General Chemistry, Chemical sciences, Engineering
Abstract

Through mechanistic work and rational design, we have developed the fastest organometallic abiotic Cys bioconjugation. As a result, the developed organometallic Au(III) bioconjugation reagents enable selective labeling of Cys moieties down to picomolar concentrations and allow for the rapid construction of complex heterostructures from peptides, proteins, and oligonucleotides. This work showcases how organometallic chemistry can be interfaced with biomolecules and lead to a range of reactivities that are largely unmatched by classical organic chemistry tools.

Published
2024

2. Visible-Light-Induced Olefin Activation Using 3D Aromatic Boron-Rich Cluster Photooxidants

Author

Messina, Marco S, Axtell, Jonathan C, Wang, Yiqun, Chong, Paul, Wixtrom, Alex I, Kirlikovali, Kent O, Upton, Brianna M, Hunter, Bryan M, Shafaat, Oliver S, Khan, Saeed I, Winkler, Jay R, Gray, Harry B, Alexandrova, Anastassia N, Maynard, Heather D, and Spokoyny, Alexander M

Subjects
Inorganic Chemistry, Chemical Sciences, Physical Chemistry, Boron Compounds, Electron Transport, Light, Models, Molecular, Molecular Structure, Oxidants, Oxidation-Reduction, Photochemical Processes, Polyenes, Polymerization, Polymers, General Chemistry, Chemical sciences, Engineering
Abstract

We report a discovery that perfunctionalized icosahedral dodecaborate clusters of the type B12(OCH2Ar)12 (Ar = Ph or C6F5) can undergo photo-excitation with visible light, leading to a new class of metal-free photooxidants. Excitation in these species occurs as a result of the charge transfer between low-lying orbitals located on the benzyl substituents and an unoccupied orbital delocalized throughout the boron cluster core. Here we show how these species, photo-excited with a benchtop blue LED source, can exhibit excited-state reduction potentials as high as 3 V and can participate in electron-transfer processes with a broad range of styrene monomers, initiating their polymerization. Initiation is observed in cases of both electron-rich and electron-deficient styrene monomers at cluster loadings as low as 0.005 mol%. Furthermore, photo-excitation of B12(OCH2C6F5)12 in the presence of a less activated olefin such as isobutylene results in the production of highly branched poly(isobutylene). This work introduces a new class of air-stable, metal-free photo-redox reagents capable of mediating chemical transformations.

Published
2016

5. Organometallic Chemistry Tools for Building Biologically Relevant Nanoscale Systems

Author

Tilden, James A. R., Doud, Evan A., Montgomery, Hayden R., Maynard, Heather D., and Spokoyny, Alexander M.

Abstract

The recent emergence of organometallic chemistry for modification of biomolecular nanostructures has begun to rewrite the long-standing assumption among practitioners that small-molecule organometallics are fundamentally incompatible with biological systems. This Perspective sets out to clarify some of the existing misconceptions by focusing on the growing organometallic toolbox for biomolecular modification. Specifically, we highlight key organometallic transformations in constructing complex biologically relevant systems on the nanomolecular scale, and the organometallic synthesis of hybrid nanomaterials composed of classical nanomaterial components combined with biologically relevant species. As research progresses, many of the challenges associated with applying organometallic chemistry in this context are rapidly being reassessed. Looking to the future, the growing utility of organometallic transformations will likely make them more ubiquitous in the construction and modification of biomolecular nanostructures.

Published
2024
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14. Development of a Grp94 inhibitor.

Author

Duerfeldt, Adam S., Peterson, Laura B., Maynard, Jason C., Chun Leung Ng, Eletto, Daviae, Ostrovsky, Olga, Shinogle, Heather E., Moore, David S., Argon, Yair, Nicchitta, Christopher V., and Blagg, Brian S. J.

Published
2012
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