A5015839834- Chemical Synthesis and Analysis
- Advanced Synthetic Organic Chemistry
- Porphyrin and Phthalocyanine Chemistry
- Chemical synthesis and alkaloids
- Chemical Synthesis and Reactions
- Asymmetric Synthesis and Catalysis
- Advanced biosensing and bioanalysis techniques
- Oxidative Organic Chemistry Reactions
- Cancer therapeutics and mechanisms
- Innovative Microfluidic and Catalytic Techniques Innovation
- Synthetic Organic Chemistry Methods
- Carbohydrate Chemistry and Synthesis
- Metal-Catalyzed Oxygenation Mechanisms
- Mycobacterium research and diagnosis
- Molecular Sensors and Ion Detection
- Alkaloids: synthesis and pharmacology
- Magnetism in coordination complexes
- Synthesis and pharmacology of benzodiazepine derivatives
- Quinazolinone synthesis and applications
- Asymmetric Hydrogenation and Catalysis
- Analytical Chemistry and Chromatography
- Ionic liquids properties and applications
- Nanomaterials for catalytic reactions
- Supramolecular Self-Assembly in Materials
- Bioactive Compounds and Antitumor Agents
Eli Lilly (United States)
2016-2022
Vanderbilt University
2015-2018
John Jay College of Criminal Justice
2018
North Carolina State University
2011-2016
Moscow State University of Fine Chemical Technologies
2006-2008
Moscow Architectural Institute
2007
Lomonosov Moscow State University
2006
The large-scale manufacture of complex synthetic peptides is challenging due to many factors such as manufacturing risk (including failed product specifications) well processes that are often low in both yield and overall purity. To overcome these liabilities, a hybrid solid-phase peptide synthesis/liquid-phase synthesis (SPPS/LPPS) approach was developed for the tirzepatide. Continuous real-time analytical monitoring ensured production high-quality material, while nanofiltration provided...
Highly stereocontrolled: The total synthesis of frog alkaloid (−)-205B features a chiral N-acylpyridinium salt reaction and an unprecedented trifluoroacetic anhydride mediated addition allylstannane to vinylogous amide. core was assembled using Tsuji–Trost allylic amination ring-closing metathesis. TIPS=triisopropylsilyl. Detailed facts importance specialist readers are published as "Supporting Information". Such documents peer-reviewed, but not copy-edited or typeset. They made available...
Abstract Herein, a one‐pot liquid phase peptide synthesis featuring iterative addition of amino acids to “nanostar” support, with organic solvent nanofiltration (OSN) for isolation the growing after each cycle is reported. A consists coupling, Fmoc removal, then sieving out reaction by‐products via in reactor‐separator, or synthesizer apparatus where no material transfers are required between cycles. The three‐armed and monodisperse nanostar facilitates both efficient real‐time monitoring...
This study focused on investigating diketopiperazine (DKP) and the formation of associated double-amino-acid deletion impurities during linear solid-phase peptide synthesis (SPPS) tirzepatide (TZP). We identified that DKP primarily occurred Fmoc-deprotection reaction post-coupling aging unstable Fmoc-Pro-Pro-Ser-resin active pharmaceutical ingredient (API) intermediate. Similar phenomena have also been observed for other TZP intermediates contain a penultimate proline amino acid, such as...
A stereoselective aza-Henry reaction between an arylnitromethane and Boc-protected aryl aldimine using a homogeneous Brønsted acid–base catalyst was translated from batch format to automated intermittent-flow process. This work demonstrates the advantages of novel setup with product crystallization slow reagent addition which is not amenable standard continuous equipment: plug flow tube reactor (PFR) or stirred tank (CSTR). significant benefit this strategy integration organocatalytic...
Concise and highly stereocontrolled total syntheses of racemic enantiopure frog alkaloid 205B (1) were accomplished in 11 steps from 4-methoxypyridines 6 7 overall yields 8 8%, respectively. The assembly the core natural product relies on a stereoselective Tsuji-Trost allylic amination reaction ring-closing metathesis. synthesis features use an N-acylpyridinium salt to introduce first stereocenter unprecedented trifluoroacetic anhydride-mediated addition allylstannane vinylogous amide with...
The synthetic utility of the aza-Henry reaction can be diminished on scale by potential hazards associated with use peracid to prepare nitroalkane substrates, and nitroalkanes themselves. In response, a continuous scalable chemistry platform aliphatic on-demand is reported, using oxidation oximes peracetic acid direct intermediate in an reaction. A uniquely designed pipes-in-series plug flow tube reactor addresses range process challenges including stability safe handling peroxides...
Herein is described an original approach to access a tricyclic framework of the lepadiformine-type alkaloids. A Grignard/N-acylpyridinium salt reaction 4-methoxytetrahydroquinoline key carbon–carbon bond-forming step that was used establish desired absolute stereochemistry at C2 position target alkaloid. The synthesis features allylation with N-acyliminium ion set C10 quaternary stereocenter, mild dissolving-metal cleavage hindered phenyl carbamates, and aminoiodocyclization form pyrrolidine...
Hoch stereokontrolliert verlief die Totalsynthese der Titelverbindung, in eine Reaktion mit einem chiralen N-Acylpyridinium-Salz, neuartige, durch Trifluoressigsäureanhydrid vermittelte Addition eines Allylstannans an ein vinyloges Amid sowie allylische Tsuji-Trost-Aminierung und Ringschlussmetathese für den Aufbau des zentralen Gerüsts genutzt wurden. TIPS = Triisopropylsilyl. Detailed facts of importance to specialist readers are published as "Supporting Information". Such documents...
Abstract Herein, a one‐pot liquid phase peptide synthesis featuring iterative addition of amino acids to “nanostar” support, with organic solvent nanofiltration (OSN) for isolation the growing after each cycle is reported. A consists coupling, Fmoc removal, then sieving out reaction by‐products via in reactor‐separator, or synthesizer apparatus where no material transfers are required between cycles. The three‐armed and monodisperse nanostar facilitates both efficient real‐time monitoring...
Mitomycin C (MC) is an anticancer agent that alkylates DNA to form monoadducts and interstrand cross-links. Decarbamoylmitomycin (DMC) analogue of MC lacking the carbamate on C10. The major adducts isolated from treatment culture cells with DMC are N