Increasing Rates of Reaction:  Microwave-Assisted Organic Synthesis for Combinatorial Chemistry

Lew, Amy; Krutzik, Peter O.; Hart, Marieke van der; Chamberlin, A. Richard

doi:10.1021/cc010048o

Cited by 370 publications

(153 citation statements)

References 39 publications

(61 reference statements)

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“…Early examples of SPOS under controlled microwave conditions [12] typically involved the use of microwaves in one single step to either attach or cleave material onto or off the resin. A study published in 2001 demonstrated that hightemperature microwave heating (200 8C) can be effectively employed to attach aromatic carboxylic acids to chloromethylated polystyrene resins (Merrifield and Wang) by the cesium carbonate method (Scheme 43).…”

Section: Methodsmentioning

confidence: 99%

“…Earlier examples of controlled MAOS are limited and can be found in previous review articles and books. [4][5][6][7][8][9][10][11][12][13][14][15][16] 2.2. Transition-Metal-Catalyzed C À C Bond Formations…”

Section: Scope and Organization Of The Reviewmentioning

confidence: 99%

“…[4][5][6][7][8][9][10][11][12][13][14][15][16] Conventional cycloaddition reactions require, in many cases, the use of harsh conditions such as high temperatures and long reaction times, but they can be performed with great success with the aid of Scheme 29. Synthesis of benzoxazoles, [167] oxazolidines, [168,169] and benzothiazoles, [170] 1,3-dipolar cycloaddition reaction to form triazoles, [171] and [3 + 2] cycloadditions of azomethine ylides and maleimide.…”

Section: Cycloaddition Reactionsmentioning

confidence: 99%

“…Therefore, many academic and industrial research groups are already using MAOS as a forefront technology for rapid optimization of reactions, for the efficient synthesis of new chemical entities, and for discovering and probing new chemical reactivity. A large number of review articles [4][5][6][7][8][9][10][11][12][13] and several books [14][15][16] provide extensive coverage of the subject. The aim of this Review is to highlight some of the most recent applications and trends in microwave synthesis, and to discuss the impact and future potential of this technology.…”

Section: Introductionmentioning

confidence: 99%

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Controlled Microwave Heating in Modern Organic Synthesis

2004

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Although fire is now rarely used in synthetic chemistry, it was not until Robert Bunsen invented the burner in 1855 that the energy from this heat source could be applied to a reaction vessel in a focused manner. The Bunsen burner was later superseded by the isomantle, oil bath, or hot plate as a source for applying heat to a chemical reaction. In the past few years, heating and driving chemical reactions by microwave energy has been an increasingly popular theme in the scientific community. This nonclassical heating technique is slowly moving from a laboratory curiosity to an established technique that is heavily used in both academia and industry. The efficiency of “microwave flash heating” in dramatically reducing reaction times (from days and hours to minutes and seconds) is just one of the many advantages. This Review highlights recent applications of controlled microwave heating in modern organic synthesis, and discusses some of the underlying phenomena and issues involved.

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Section: Methodsmentioning

confidence: 99%

Section: Scope and Organization Of The Reviewmentioning

confidence: 99%

Section: Cycloaddition Reactionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Controlled Microwave Heating in Modern Organic Synthesis

2004

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“…The first demonstration of microwave-assisted organic synthesis was made independently in the research laboratories of Giguere [25] and Gedye [26]. Since then, microwave irradiation has been used to assist in various chemical reactions [27,28]. There were reports of using microwave irradiation for the hydrolysis of peptides and proteins.…”

mentioning

confidence: 99%

Microwave-assisted acid hydrolysis of proteins combined with liquid chromatography MALDI MS/MS for protein identification

Zhong

Marcus

2005

J. Am. Soc. Mass Spectrom.

149

142

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Simple and efficient digestion of proteins, particularly hydrophobic membrane proteins, is of significance for comprehensive proteome analysis using the bottom-up approach. We report a microwave-assisted acid hydrolysis (MAAH) method for rapid protein degradation for peptide mass mapping and tandem mass spectrometric analysis of peptides for protein identification. It uses 25% trifluoroacetic acid (TFA) aqueous solution to dissolve or suspend proteins, followed by microwave irradiation for 10 min. This detergent-free method generates peptide mixtures that can be directly analyzed by liquid chromatography (LC) matrix-assisted laser desorption ionization (MALDI) mass spectrometry (MS) without the need of extensive sample cleanup. LC-MALDI MS/MS analysis of the hydrolysate from 5 g of a model transmembrane protein, bacteriorhodopsin, resulted in almost complete sequence coverage by the peptides detected, including the identification of two posttranslational modification sites. Cleavage of peptide bonds inside all seven transmembrane domains took place, generating peptides of sizes amenable to MS/MS to determine possible sequence errors or modifications within these domains. Cleavage specificity, such as glycine residue cleavage, was observed. Terminal peptides were found to be present in relatively high abundance in the hydrolysate, particularly when low concentrations of proteins were used for MAAH. It was shown that these peptides could still be detected from MAAH of bacteriorhodopsin at a protein concentration of 1 ng/ l or 37 fmol/ l. To evaluate the general applicability of this method, it was applied to identify proteins from a membrane protein enriched fraction of cell lysates of human breast cancer cell line MCF7. With one-dimensional LC-MALDI MS/MS, a total of 119 proteins, including 41 membrane-associated or membrane proteins containing one to 12 transmembrane domains, were identified by MS/MS database searching based on matches of at least two peptides to a protein. (J Am Soc Mass Spectrom 2005, 16, 471-481)

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