Search Results - "Lipton, Mark A"

Reorganization of the Organic Chemistry Curriculum to Improve Student Outcomes by Lipton, Mark A

“…The material of a standard second-year undergraduate organic chemistry class has been reorganized and reframed to emphasize the mechanistic connections between…”
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Synthesis of N-Fmoc-(2S,3S,4R)-3,4-dimethylglutamine: An Application of Lanthanide-Catalyzed Transamidation by Çalimsiz, Selçuk, Lipton, Mark A

“…N-Fmoc-(2S,3S,4R)-3,4-dimethylglutamine (6) was synthesized from tert-butyl N-Boc-(2S,3S,4R)-dimethylpyroglutamate (13). This synthesis involved selective…”
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Solid-Phase Total Synthesis and Structure Proof of Callipeltin B by Krishnamoorthy, Ravi, Vazquez-Serrano, Leslie D, Turk, Jeffrey A, Kowalski, Jennifer A, Benson, Alan G, Breaux, Nneka T, Lipton, Mark A

“…The cytotoxic, cyclic heptadepsipeptide, natural product callipeltin B was synthesized on a solid-phase support in 15% overall yield. Comparison of the 1H NMR…”
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Chirality determination of unusual amino acids using precolumn derivatization and liquid chromatography–electrospray ionization mass spectrometry by Hess, Sonja, Gustafson, Kirk R, Milanowski, Dennis J, Alvira, Edgardo, Lipton, Mark A, Pannell, Lewis K

“…Unusual amino acids such as β-methoxytyrosine (β-MeOTyr), allo-threonine ( allo-Thr) and allo-isoleucine ( allo-Ile) were derivatized with…”
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Synthesis and spectroscopic correlation of the diastereoisomers of 2,3-dihydroxy-2,6,8-trimethyldeca-(4 Z,6 E)-dienoic acid: implications for the structures of papuamides A–D and mirabamides A–D by Ramamoorthy, Gurusankar, Acevedo, Cristina M., Alvira, Edgardo, Lipton, Mark A.

“…All 4 diastereomeric possibilities for the 2,3-dihydroxy-2,6,8-trimethyldeca-(4 Z,6 E)-dienoic acid (Dhtda) residue, found in the cyclic depsipeptide natural…”
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Solid-Phase Synthesis and Configurational Reassigment of Callipeltin E. Implications for the Structures of Callipeltins A and B by Çalimsiz, Selçuk, Morales Ramos, Ángel I, Lipton, Mark A

“…Two possible isomers of the natural product callipeltin E (1, 5) were synthesized by using an Fmoc-based solid-phase strategy in 7 steps, in 20% and 26%…”
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Facile and Efficient Guanylation of Amines Using Thioureas and Mukaiyama's Reagent by Yong, Yaw Fui, Kowalski, Jennifer A, Lipton, Mark A

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An Optimized Preparation of 1,1-Dimethylallyl Esters and Their Application to Solid-Phase Peptide Synthesis by Hostetler, Matthew A, Lipton, Mark A

“…A one-step preparation of 1,1-dimethylallyl (DMA) esters was optimized for the C-terminal protection of a range of Fmoc-protected amino acids. This preparation…”
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A Convenient, General Synthesis of 1,1-Dimethylallyl Esters as Protecting Groups for Carboxylic Acids by Sedighi, Minoo, Lipton, Mark A

“…Carboxylic acids were converted in high yield to their 1,1-dimethylallyl (DMA) esters in two steps. Palladium-catalyzed deprotection of DMA esters was shown to…”
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The acid-catalyzed hydrolysis of an α-pinene-derived organic nitrate: kinetics, products, reaction mechanisms, and atmospheric impact by Rindelaub, Joel D., Borca, Carlos H., Hostetler, Matthew A., Slade, Jonathan H., Lipton, Mark A., Slipchenko, Lyudmila V., Shepson, Paul B.

“…The production of atmospheric organic nitrates (RONO2) has a large impact on air quality and climate due to their contribution to secondary organic aerosol and…”
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Synthesis and cytotoxicity of desmethoxycallipeltin B: Lack of a quinone methide for the cytotoxicity of callipeltin B by Krishnamoorthy, Ravi, Richardson, Brooke L., Lipton, Mark A.

“…The desmethoxy analogue of the cytotoxic, cyclic depsipeptide callipeltin B was synthesized to evaluate the role of its β-MeOTyr residue. The IC 50 of…”
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Asymmetric Synthesis of Four Diastereomers of 3-Hydroxy-2,4,6-trimethylheptanoic Acid:  Proof of Configurational Assignment by Turk, Jeffrey A, Visbal, Gonzalo S, Lipton, Mark A

“…Four unique diastereomers of 3-hydroxy-2,4,6-trimethylheptanoic acid(2R,3R,4R), (2S,3R,4R), (2S,3R,4S), and (2R,3R,4S)the fatty acid component of callipeltin…”
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Synthesis of the Unnatural Amino Acid AGDHE, a Constituent of the Cyclic Depsipeptides Callipeltins A and D by Thoen, Jason C, Morales-Ramos, Ángel I, Lipton, Mark A

“…The novel amino acid residue (2R,3R,4S)-4-amido-7-guanidino-2,3-dihydroxyheptanoic acid (AGDHE, 3), a constituent of the cyclic depsipeptides callipeltins A…”
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Conformations of Thioamide-Containing Dipeptides:  A Computational Study by Artis, Dean R, Lipton, Mark A

“…Four model dipeptides, Ac-ψ[CSNH]-Gly-NHMe, Ac-Gly-ψ[CSNH]-NHMe, Ac-ψ[CSNH]-Ala-NHMe, and Ac-Ala-ψ[CSNH]-NHMe, each containing a thioamide bond, were studied…”
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A Density Functional Molecular Orbital Study of the C2−C7 and C2−C6 Cyclization Pathways of 1,2,4-Heptatrien-6-ynes. The Role of Benzannulation by Wenthold, Paul G, Lipton, Mark A

“…The electronic factors influencing the competition between C2−C7 (Myers−Saito) and C2−C6 (Schmittel) cyclizations of 1,2,4-heptatrien-6-yne and…”
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Death effects of reveromycin A in normal and disease‐associated cells of the joint by Svrcina, Haley, Greer, Austin, Baker, Seth, Smith, Morgan, Martinez, Patricia, Granger, Nathan, Thomas, Natassja, Miller, Jaylin, Steinke, Ellen, Davitt, Kelsey, Sloane, Emily, Nugent, Lauren, Sabo, Ryan, Williams, Calli, Lipton, Mark A., Jones, Daniel

“…Earlier work in our laboratory demonstrated that naturally occurring reveromycin A (Rev A) causes apoptosis in osteoclasts without accompanying necrosis. Rev A…”
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Solid-Phase Synthesis of Callipeltin D. Stereochemical Confirmation of the Unnatural Amino Acid AGDHE by Cranfill, David C, Morales-Ramos, Ángel I, Lipton, Mark A

“…The lipopeptide callipeltin D (1) was synthesized using an Fmoc-based solid-phase strategy in seven steps and 35% overall yield. The 1H NMR of synthetic 1…”
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“Concerted” Transition State, Stepwise Mechanism. Dynamics Effects in C2-C6 Enyne Allene Cyclizations by Bekele, Tefsit, Christian, Chad F, Lipton, Mark A, Singleton, Daniel A

“…The C2−C6 (Schmittel)/ene cyclization of enyne-allenes is studied by a combination of kinetic isotope effects, theoretical calculations, and dynamics…”
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Design, synthesis, biological and structural evaluation of functionalized resveratrol analogues as inhibitors of quinone reductase 2 by St. John, Sarah E., Jensen, Katherine C., Kang, SooSung, Chen, Yafang, Calamini, Barbara, Mesecar, Andrew D., Lipton, Mark A.

“…Resveratrol (3,5,4′-trihydroxylstilbene) has been proposed to elicit a variety of positive health effects including protection against cancer and…”
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Enantio- and Diastereoselective Synthesis of (R,R)-β-Methoxytyrosine by Cranfill, David C, Lipton, Mark A

“…The nonproteinogenic amino acid (2R,3R)-β-methoxytyrosine, a constituent of several cyclic depsipeptide natural products, was synthesized in protected form (8)…”
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