A flow reactor process for the synthesis of peptides utilizing immobilized reagents, scavengers and catch and release protocols

Baxendale, Ian R.; Ley, Steven V.; Smith, Christopher D.; Tranmer, Geoffrey K.

doi:10.1039/b612197g

Cited by 98 publications

(68 citation statements)

References 15 publications

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“…It was discovered that when the dimethyll -tartrate and trimethyl orthoformate were premixed, rapid formation of an intermediate diacetal occurred, which was observed using the ReactIR flow cell ( Scheme 17 ). This proved to be an important observation and optimization of Guanadine library [80] Thiazole library [79] Oxazole library [83] Grossamide [81] Zolpidem [72] Meclinertant SR 48692 [74] Casein Kinase Inhibitors library [77] Aminopyrrolidines [78] Polypeptides [82] Scheme 15 A range of other targeted structures achieved using multi-step flow synthesis.…”

Section: Reaction Monitoring With In-line Diagnosticsmentioning

confidence: 99%

Flow chemistry approaches directed at improving chemical synthesis

Baxendale

Brocken

Mallia

2013

Green Processing and Synthesis

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Flow synthesis offers many advantages when applied to the processing of difficult or dangerous chemical transformations. Furthermore, continuous production allows for rapid scale up of reactions without significant redevelopment of the routes. Importantly, it can also provide a versatile platform from which to build integrated multi-step transformations, delivering more advanced chemical architectures. The construction of multi-purpose micro and meso flow systems, that utilize in-line purification and diagnostic capabilities, creates a scenario of seamless connectivity between sequential steps of a longer chemical sequence. In this mini perspective, we will discuss our experience of target orientated multi-step synthesis as presented at the recent inaugural meeting of LEGOMEDIC at Namar University, Belgium.

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Section: Reaction Monitoring With In-line Diagnosticsmentioning

confidence: 99%

Flow chemistry approaches directed at improving chemical synthesis

Baxendale

Brocken

Mallia

2013

Green Processing and Synthesis

Self Cite

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“…The ready ability to monitor each transformation in real time enables the construction of telescoped sequences of multiple synthetic steps into a single continuous operation, thereby permitting the preparation of complex targets within a drastically reduced timeframe. [107] Once the technological capability has been developed to prepare high-quality molecular entities comprising all the desired members of a compound library in an on-demand fashion, the only question that remains is what to synthesise next. This question can be addressed in an iterative fashion by using the results from the testing of the initial library to determine the next chemical series.…”

Section: Emerging Technologies: a Personal Perspectivementioning

confidence: 99%

Pharmaceutical Strategy and Innovation: An Academics Perspective

et al. 2007

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The pharmaceutical industry is under increasing pressure on many fronts, from investors requiring larger returns to consumer groups and health authorities demanding cheaper and safer drugs. It is also feeling additional pressure from the infringement upon its profit margins by generic drug producers. Many companies are aggressively pursuing outsourcing contracts in an attempt to counter many of the financial pressures and streamline their operations. At the same time, the productivity of the pharmaceutical industry at its science base is being questioned in terms of the number of products and the timeframes required for each company to deliver them to market. This has generated uncertainties regarding the current corporate strategies that have been adopted and the levels of innovation being demonstrated. In this essay we discuss these topics in the context of the global pharmaceutical market, investigating the basis for many of these issues and highlighting the hurdles the industry needs to overcome, especially as they relate to the chemical sciences.

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“…Recent marked progress in micro-flow technology1314151617181920 has enabled precise control of the reaction time (<1 s) and temperature212223. We have studied micro-flow acylations2425 and recently reported micro-flow amide bond formation using a high atom economy and an inexpensive coupling agent, triphosgene26.…”

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confidence: 99%

Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation

et al. 2016

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Feglymycin is a naturally occurring, anti-HIV and antimicrobial 13-mer peptide that includes highly racemizable 3,5-dihydroxyphenylglycines (Dpgs). Here we describe the total synthesis of feglymycin based on a linear/convergent hybrid approach. Our originally developed micro-flow amide bond formation enabled highly racemizable peptide chain elongation based on a linear approach that was previously considered impossible. Our developed approach will enable the practical preparation of biologically active oligopeptides that contain highly racemizable amino acids, which are attractive drug candidates.

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A flow reactor process for the synthesis of peptides utilizing immobilized reagents, scavengers and catch and release protocols

Cited by 98 publications

References 15 publications

Flow chemistry approaches directed at improving chemical synthesis

Flow chemistry approaches directed at improving chemical synthesis

Pharmaceutical Strategy and Innovation: An Academics Perspective

Total synthesis of feglymycin based on a linear/convergent hybrid approach using micro-flow amide bond formation

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