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Research Output 1998 2019

2019

Axial shielding of Pd(II) complexes enables perfect stereoretention in Suzuki-Miyaura cross-coupling of Csp 3 boronic acids

Lehmann, J. W., Crouch, I. T., Blair, D. J., Trobe, M., Wang, P., Li, J. & Burke, M., Dec 1 2019, In : Nature communications. 10, 1, 1263.

Research output: Contribution to journalArticle

Open Access
Boronic Acids
cross coupling
Shielding
shielding
acids

Modular Syntheses of Phenanthroindolizidine Natural Products

Jo, Y. I., Burke, M. D. & Cheon, C. H., Jun 7 2019, In : Organic Letters. 21, 11, p. 4201-4204 4 p.

Research output: Contribution to journalArticle

Boronic Acids
Vanadium
Biological Products
Bromides
Alkaloids

Small-molecule ion channels increase host defences in cystic fibrosis airway epithelia

Muraglia, K. A., Chorghade, R. S., Kim, B. R., Tang, X. X., Shah, V. S., Grillo, A. S., Daniels, P. N., Cioffi, A. G., Karp, P. H., Zhu, L., Welsh, M. J. & Burke, M. D., Mar 21 2019, In : Nature. 567, 7748, p. 405-408 4 p.

Research output: Contribution to journalLetter

Cystic Fibrosis Transmembrane Conductance Regulator
Ion Channels
Cystic Fibrosis
Amphotericin B
Epithelium
2018

FAM210B is an erythropoietin target and regulates erythroid heme synthesis by controlling mitochondrial iron import and ferrochelatase activity

Yien, Y. Y., Shi, J., Chen, C., Cheung, J. T. M., Grillo, A. S., Shrestha, R., Li, L., Zhang, X., Kafina, M. D., Kingsley, P. D., King, M. J., Ablain, J., Li, H., Zon, L. I., Palis, J., Burke, M. D., Bauer, D. E., Orkin, S. H., Koehler, C. M., Phillips, J. D. & 4 others, Kaplan, J., Ward, D. M., Lodish, H. F. & Paw, B. H., Jan 1 2018, In : Journal of Biological Chemistry. 293, 51, p. 19797-19811 15 p.

Research output: Contribution to journalArticle

Ferrochelatase
Erythropoietin
Heme
Iron
Erythropoiesis

Peridinin Is an Exceptionally Potent and Membrane-Embedded Inhibitor of Bilayer Lipid Peroxidation

Haley, H. M. S., Hill, A. G., Greenwood, A. I., Woerly, E. M., Rienstra, C. & Burke, M., Nov 14 2018, In : Journal of the American Chemical Society. 140, 45, p. 15227-15240 14 p.

Research output: Contribution to journalArticle

Lipid bilayers
Endothelial cells
inhibitor
lipid
Lipid Peroxidation

Solid-State NMR of highly 13 C-enriched cholesterol in lipid bilayers

Della Ripa, L. A., Petros, Z. A., Cioffi, A. G., Piehl, D. W., Courtney, J. M., Burke, M. D. & Rienstra, C. M., Apr 1 2018, In : Methods. 138-139, p. 47-53 7 p.

Research output: Contribution to journalArticle

Lipid bilayers
Lipid Bilayers
Sterols
Biophysical Phenomena
Biochemical Phenomena

The Molecular Industrial Revolution: Automated Synthesis of Small Molecules

Trobe, M. & Burke, M. D., Apr 9 2018, In : Angewandte Chemie - International Edition. 57, 16, p. 4192-4214 23 p.

Research output: Contribution to journalReview article

3D printers
Automation
Molecules
Innovation
Direction compound

Towards the generalized iterative synthesis of small molecules

Lehmann, J. W., Blair, D. J. & Burke, M., Jan 1 2018, In : Nature Reviews Chemistry. 2, 2, 0115.

Research output: Contribution to journalReview article

Molecules
Tall buildings
Biological Products
Macromolecules
Drug products
2017

Restored iron transport by a small molecule promotes absorption and hemoglobinization in animals

Grillo, A. S., SantaMaria, A. M., Kafina, M. D., Cioffi, A. G., Huston, N. C., Han, M., Seo, Y. A., Yien, Y. Y., Nardone, C., Menon, A. V., Fan, J., Svoboda, D. C., Anderson, J. B., Hong, J. D., Nicolau, B. G., Subedi, K., Gewirth, A. A., Wessling-Resnick, M., Kim, J., Paw, B. H. & 1 others, Burke, M., May 12 2017, In : Science. 356, 6338, p. 608-616 9 p.

Research output: Contribution to journalArticle

Iron
Zebrafish
Biological Products
Carrier Proteins
Membrane Proteins

The natural productome

Palazzolo, A. M. E., Simons, C. L. W. & Burke, M. D., May 30 2017, In : Proceedings of the National Academy of Sciences of the United States of America. 114, 22, p. 5564-5566 3 p.

Research output: Contribution to journalComment/debate

2016

MIDA boronates are hydrolysed fast and slow by two different mechanisms

Gonzalez, J. A., Ogba, O. M., Morehouse, G. F., Rosson, N., Houk, K. N., Leach, A. G., Cheong, P. H. Y., Burke, M. D. & Lloyd-Jones, G. C., Nov 1 2016, In : Nature Chemistry. 8, 11, p. 1067-1075 9 p.

Research output: Contribution to journalArticle

Boronic Acids
Hydrolysis
Esters
Acids
Water

Our Path to Less Toxic Amphotericins

Endo, M. M., Cioffi, A. G. & Burke, M. D., Feb 12 2016, In : Synlett. 27, 3, p. 337-354 18 p.

Research output: Contribution to journalArticle

Poisons
Amphotericin B
Ergosterol
Biological Products
Ion Channels
2015

C3-OH of Amphotericin B Plays an Important Role in Ion Conductance

Davis, S. A., Della Ripa, L. A., Hu, L., Cioffi, A. G., Pogorelov, T. V., Rienstra, C. M. & Burke, M. D., Dec 9 2015, In : Journal of the American Chemical Society. 137, 48, p. 15102-15104 3 p.

Research output: Contribution to journalArticle

Amphotericin B
Ion Channels
Ions
ion
Hydroxyl Radical

From Synthesis to Function via Iterative Assembly of N-Methyliminodiacetic Acid Boronate Building Blocks

Li, J., Grillo, A. S. & Burke, M. D., Jul 22 2015, In : Accounts of chemical research. 48, 8, p. 2297-2307 11 p.

Research output: Contribution to journalArticle

Molecules
Biological Products
Polyenes
Poisons
Aldehydes

Nontoxic antimicrobials that evade drug resistance

Davis, S. A., Vincent, B. M., Endo, M. M., Whitesell, L., Marchillo, K., Andes, D. R., Lindquist, S. & Burke, M. D., Jul 20 2015, In : Nature chemical biology. 11, 7, p. 481-487 7 p.

Research output: Contribution to journalArticle

Amphotericin B
Microbial Drug Resistance
Poisons
Ergosterol
Sterols

Restored physiology in protein-deficient yeast by a small molecule channel

Cioffi, A. G., Hou, J., Grillo, A. S., Diaz, K. A. & Burke, M. D., Aug 19 2015, In : Journal of the American Chemical Society. 137, 32, p. 10096-10099 4 p.

Research output: Contribution to journalArticle

Fungal Proteins
Physiology
yeast
physiology
Proteins

Synthesis of many different types of organic small molecules using one automated process

Li, J., Ballmer, S. G., Gillis, E. P., Fujii, S., Schmidt, M. J., Palazzolo, A. M. E., Lehmann, J. W., Morehouse, G. F. & Burke, M. D., Mar 13 2015, In : Science. 347, 6227, p. 1221-1226 6 p.

Research output: Contribution to journalArticle

Biological Products
2014

Amphotericin forms an extramembranous and fungicidal sterol sponge

Anderson, T. M., Clay, M. C., Cioffi, A. G., Diaz, K. A., Hisao, G. S., Tuttle, M. D., Nieuwkoop, A. J., Comellas, G., Maryum, N., Wang, S., Uno, B. E., Wildeman, E. L., Gonen, T., Rienstra, C. M. & Burke, M. D., May 2014, In : Nature chemical biology. 10, 5, p. 400-406 7 p.

Research output: Contribution to journalArticle

Porifera
Amphotericin B
Sterols
Yeasts
Lipid Bilayers

Synthesis of most polyene natural product motifs using just 12 building blocks and one coupling reaction

Woerly, E. M., Roy, J. & Burke, M. D., Jun 2014, In : Nature Chemistry. 6, 6, p. 484-491 8 p.

Research output: Contribution to journalArticle

Polyenes
Biological Products
Molecules
Oligosaccharides
Oligonucleotides
2013
Organic Chemistry
Creativity
Alkenes
Molecules
N-methyliminodiacetic acid

C2′-OH of amphotericin B plays an important role in binding the primary sterol of human cells but not yeast cells

Wilcock, B. C., Endo, M. M., Uno, B. E. & Burke, M. D., Jun 12 2013, In : Journal of the American Chemical Society. 135, 23, p. 8488-8491 4 p.

Research output: Contribution to journalArticle

sterol
Cholesterol
Amphotericin B
Sterols
Yeast
2012

A general solution for the 2-pyridyl problem

Dick, G. R., Woerly, E. M. & Burke, M. D., Mar 12 2012, In : Angewandte Chemie - International Edition. 51, 11, p. 2667-2672 6 p.

Research output: Contribution to journalArticle

diethanolamine
Boranes
Dimethylformamide
Palladium
Air

Amphotericin primarily kills yeast by simply binding ergosterol

Gray, K. C., Palacios, D. S., Dailey, I., Endo, M. M., Uno, B. E., Wilcock, B. C. & Burke, M. D., Feb 14 2012, In : Proceedings of the National Academy of Sciences of the United States of America. 109, 7, p. 2234-2239 6 p.

Research output: Contribution to journalArticle

Ergosterol
Amphotericin B
Yeasts
Ion Channels
Biological Products

Electronic tuning of site-selectivity

Wilcock, B. C., Uno, B. E., Bromann, G. L., Clark, M. J., Anderson, T. M. & Burke, M. D., Dec 1 2012, In : Nature Chemistry. 4, 12, p. 996-1003 8 p.

Research output: Contribution to journalArticle

Tuning
Acylation
Amphotericin B
Biological Products
Ion Channels
2011

(Z)-(2-bromovinyl)-MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis

Woerly, E. M., Struble, J. R., Palyam, N., O'Hara, S. P. & Burke, M. D., Jun 17 2011, In : Tetrahedron. 67, 24, p. 4333-4343 11 p.

Research output: Contribution to journalArticle

Alkenes
Molecules
N-methyliminodiacetic acid
ligand
Ligands
Cross-Linking Reagents
Acids
acid

Synthesis-enabled functional group deletions reveal key underpinnings of amphotericin B ion channel and antifungal activities

Palacios, D. S., Dailey, I., Siebert, D. M., Wilcock, B. C. & Burke, M. D., Apr 26 2011, In : Proceedings of the National Academy of Sciences of the United States of America. 108, 17, p. 6733-6738 6 p.

Research output: Contribution to journalArticle

Amphotericin B
Ion Channels
Ergosterol
Biological Products
Carboxylic Acids

Total synthesis of synechoxanthin through iterative cross-coupling

Fujii, S., Chang, S. Y. & Burke, M. D., Aug 16 2011, In : Angewandte Chemie - International Edition. 50, 34, p. 7862-7864 3 p.

Research output: Contribution to journalArticle

Carotenoids
Bioactivity
Antioxidants
Biological Products
synechoxanthin
2010

A simple and general platform for generating stereochemically complex polyene frameworks by iterative cross-coupling

Lee, S. J., Anderson, T. M. & Burke, M. D., Nov 15 2010, In : Angewandte Chemie - International Edition. 49, 47, p. 8860-8863 4 p.

Research output: Contribution to journalArticle

Polyenes
Biological Products
vacidin A

Ethynyl MIDA boronate: A readily accessible and highly versatile building block for small molecule synthesis

Struble, J. R., Lee, S. J. & Burke, M. D., Jun 26 2010, In : Tetrahedron. 66, 26, p. 4710-4718 9 p.

Research output: Contribution to journalArticle

Acetylene
Molecules
N-methyliminodiacetic acid

General method for synthesis of 2-heterocyclic N-methyliminodiacetic acid boronates

Dick, G. R., Knapp, D. M., Gillis, E. P. & Burke, M. D., May 21 2010, In : Organic Letters. 12, 10, p. 2314-2317 4 p.

Research output: Contribution to journalArticle

acids
synthesis
Bromides
bromides
Salts

Stereoretentive suzuki-miyaura coupling of haloallenes enables fully stereocontrolled access to (-)-Peridinin

Woerly, E. M., Cherney, A. H., Davis, E. K. & Burke, M. D., May 26 2010, In : Journal of the American Chemical Society. 132, 20, p. 6941-6943 3 p.

Research output: Contribution to journalArticle

Biological Products
Boronic Acids
Benchmarking
Boron
halide
2009

A general solution for unstable boronic acids: Slow-release cross-coupling from air-stable MIDA boronates

Knapp, D. M., Gillis, E. P. & Burke, M. D., May 27 2009, In : Journal of the American Chemical Society. 131, 20, p. 6961-6963 3 p.

Research output: Contribution to journalArticle

Boronic Acids
Air
Acids
acid
air

B-protected haloboronic acids for iterative cross-coupling

Ballmer, S. G., Gillis, E. P., Burke, M. D., Morton, D. & Davies, H. M. L., Dec 1 2009, In : Organic Syntheses. 86, p. 344-359 16 p.

Research output: Contribution to journalArticle

cross coupling
acids

Flexible tetracycline synthesis yields promising antibiotics

Burke, M., Feb 6 2009, In : Nature chemical biology. 5, 2, p. 77-79 3 p.

Research output: Contribution to journalShort survey

Tetracycline
Anti-Bacterial Agents
Biological Products
Bacteria

Iterative cross-coupling with MIDA boronates: Towards a general strategy for small-molecule synthesis

Gillis, E. P. & Burke, M. D., Nov 27 2009, In : Aldrichimica Acta. 42, 1, p. 17-27 11 p.

Research output: Contribution to journalArticle

Molecules
N-methyliminodiacetic acid

Vinyl MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis

Uno, B. E., Gillis, E. P. & Burke, M. D., Apr 18 2009, In : Tetrahedron. 65, 16, p. 3130-3138 9 p.

Research output: Contribution to journalArticle

Molecules
Acids
Stereoisomerism
Alkenes
Biological Products
2008

Multistep synthesis of complex boronic acids from simple MIDA boronates

Gillis, E. P. & Burke, M. D., Oct 29 2008, In : Journal of the American Chemical Society. 130, 43, p. 14084-14085 2 p.

Research output: Contribution to journalArticle

Boronic Acids
Boron
Acids
acid
Functional groups

Simple, efficient, and modular syntheses of polyene natural products via iterative cross-coupling

Suk, J. L., Gray, K. C., Paek, J. S. & Burke, M. D., Jan 16 2008, In : Journal of the American Chemical Society. 130, 2, p. 466-468 3 p.

Research output: Contribution to journalArticle

Polyenes
Biological Products
Boronic Acids
Acids
acid
2007

A post-PKS oxidation of the amphotericin B skeleton predicted to be critical for channel formation is not required for potent antifungal activity

Palacios, D. S., Anderson, T. M. & Burke, M. D., Nov 14 2007, In : Journal of the American Chemical Society. 129, 45, p. 13804-13805 2 p.

Research output: Contribution to journalArticle

Amphotericin B
Skeleton
skeleton
oxidation
Oxidation
Boronic Acids
Ligands
Nucleophiles
Molecules
Acids
2004

A Planning Strategy for Diversity-Oriented Synthesis

Burke, M. D. & Schreiber, S. L., Dec 22 2004, In : Angewandte Chemie - International Edition. 43, 1, p. 46-58 13 p.

Research output: Contribution to journalReview article

Planning
Molecules
Stereochemistry
Screening
Teaching

A synthesis strategy yielding skeletally diverse small molecules combinatorially

Burke, M., Berger, E. M. & Schreiber, S. L., Nov 3 2004, In : Journal of the American Chemical Society. 126, 43, p. 14095-14104 10 p.

Research output: Contribution to journalArticle

Skeleton
Amino Acid Sequence
folding
Molecules
Protein Folding
2003

Chemoenzymatic route to macrocyclic hybrid peptide/polyketide-like molecules

Kohli, R. M., Burke, M. D., Tao, J. & Walsh, C. T., Jun 18 2003, In : Journal of the American Chemical Society. 125, 24, p. 7160-7161 2 p.

Research output: Contribution to journalArticle

Polyketides
peptide
Peptides
Biological Products
Molecules

Generating Diverse Skeletons of Small Molecules Combinatorially

Burke, M. D., Berger, E. M. & Schreiber, S. L., Oct 24 2003, In : Science. 302, 5645, p. 613-618 6 p.

Research output: Contribution to journalArticle

Skeleton
2002

Teaching target-oriented and diversity-oriented organic synthesis at Harvard University

Burke, M. D. & Lalic, G., Jun 17 2002, In : Chemistry and Biology. 9, 5, p. 535-541 7 p.

Research output: Contribution to journalReview article

Synthetic Chemistry Techniques
Organic Chemistry
Teaching
History
Students
2001

Conformationally restricted hybrid analogues of the hormone 1α,25-dihydroxyvitamin D3: Design, synthesis, and biological evaluation

White, M. C., Burke, M., Peleg, S., Brem, H. & Posner, G. H., Jan 1 2001, In : Bioorganic and Medicinal Chemistry. 9, 7, p. 1691-1699 9 p.

Research output: Contribution to journalArticle

phosphine
Calcitriol
Hormones
Hypercalcemia
Ketones