Peptide synthesis on fluorous support

Mizuno, Mamoru; Goto, Kohtaro; Miura, Tsuyoshi; Matsuura, Takeshi; Inazu, Toshiyuki

doi:10.1016/j.tetlet.2004.03.013

Cited by 39 publications

(26 citation statements)

References 9 publications

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“…The microreactor not only allows for quick “scanning” of reaction conditions, but also for the procurement of synthetically useful amounts of peptides 6. Our report is also the first demonstration of 1) peptide couplings with tert ‐butyloxycarbonyl (Boc)‐ and 9‐fluorenylmethoxycarbonyl (Fmoc)‐protected amino acids in 1–5 minutes at temperatures as high as 120 °C, 2) the use of β 2 ‐ and β 3 ‐homoamino acid fluorides for β‐peptide couplings, and 3) the advantageous application of a C 10 H 4 F 17 ‐substituted benzylic ester protecting group in solution‐phase peptide synthesis 7–9…”

Section: Methodsmentioning

confidence: 99%

Microreactor Synthesis of β‐Peptides

et al. 2006

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LCMS analysis:LCMS analysis was performed using a Waters Symmetry ® C18 5µm column (3.9 x 150 mm) or a Waters Sunfire ® C8 5µm column (4.6 x 150 mm), using solvent systems A (20% isopropanol and 0.1% TFA in H 2 O) and B (20% isopropanol and 0.1% TFA in acetonitrile), at a flowrate of 1 mL/min. Micro reactor experiments:In all experiments a Harvard Scientific PHD 2000 syringe pump was used to simultaneously advance the syringes.Heating of the reactor was accomplished by submerging the complete reactor in an oil bath, which was heated using a thermo-couple. General procedure for reaction scanning using the micro reactor:The micro reactor was equipped with the following syringes: Before running the reactor it was rinsed with a copious amount of DMF. Before the first run the system was rinsed with 250 µL (pre-quench volume) of reaction mixture. Before every new run at a given temperature the system was equilibrated with 100 µL pre-quench reaction mixture, pumped through the reactor at the appropriate speed. Next, 3 aliquots of 25 µL (prequench volume) reaction mixture were collected, which were diluted with CH 2 Cl 2 (1 mL) and analyzed by LCMS. The LCMS traces were integrated and the product peaks were normalized vs the internal standard. This way a data-set of relative conversions was obtained.General procedure for a large scale reaction in the micro reactor:The micro reactor was equipped with the following syringes:Inlet A: 2.5 mL syringe, containing a solution of the amino acid-TFA salt (0.24 M) in DMF Inlet B: 2.5 mL syringe, containing a solution of the acid fluoride (0.48 M) in DMF

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Section: Methodsmentioning

confidence: 99%

Microreactor Synthesis of β‐Peptides

et al. 2006

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“…[26][27][28] To permit Fmoc-chemistry, 4-hydroxymethylphenoxyacetic acid (HMPA) was attached as a linker using carbodiimide/HOBt chemistry at room temperature. 23 (Scheme 3).…”

Section: Peptide Synthesismentioning

confidence: 99%

Multistep Synthesis on SU-8: Combining Microfabrication and Solid-Phase Chemistry on a Single Material

et al. 2007

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SU-8 is an epoxy-novolac resin and a well-established negative photoresist for microfabrication and microengineering. The photopolymerized resist is an extremely highly crosslinked polymer showing outstanding chemical and physical robustness with residual surface epoxy groups amenable for chemical functionalization. In this paper we describe, for the first time, the preparation and surface modification of SU-8 particles shaped as microbars, the attachment of appropriate linkers, and the successful application of these particles to multistep solid-phase synthesis leading to oligonucleotides and peptides attached in an unambiguous manner to the support surface.

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“…These heavy fluorous tags have been used in solution-phase peptide synthesis (Scheme 6). 18,19 In the synthesis of tripeptide pGlu-His-Pro-NH 2 , an excess amount of amino acid derivative was used in each coupling step. The unreacted reagent and coupling agents were removed by extraction with MeCN from the perfluorohexane (FC-72) layer.…”

Section: Scheme 5 Fluorous Tags and Peptide Synthesis With F-tmse Tagmentioning

confidence: 99%

Fluorous Chemistry for Synthesis and Purification of Biomolecules: Peptides, Oligosaccharides, Glycopeptides, and Oligonucleotides

Zhang

2007

Current Fluoroorganic Chemistry

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Fluorous chemistry has advanced well beyond the scope of biphasic catalysis and high-throughput synthesis of small molecules. This review describes the recent development of fluorous technologies in the synthesis and purification of biomolecules including peptides, oligosaccharides, glycopeptides, and oligonucleotides.Highly fluorinated (fluorous) molecules are lipophobic and hydrophobic, 1 but they have strong interaction with fluorous separation media. This unique property has been exploited for phase separation of fluorous-tagged molecules from non-fluorous molecules by liquid-liquid extraction (LLE) with fluorous solvents or by solid-phase extraction (SPE) and chromatography with fluorous silica gel. 2 In 1994 Horváth and Rábai introduced the concept of "fluorous biphasic catalysis" for catalyst recovery. 3,4 Since then, Curran group at the University of Pittsburgh, Fluorous Technologies, Inc., and others have developed a large collection of fluorous catalysts, reagents, scavengers, protecting groups for "fluorous synthesis" of small molecules. 5 ' 8 Now fluorous technologies have been applied to synthesis arid separation of biomolecules.

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Peptide synthesis on fluorous support

Cited by 39 publications

References 9 publications

Microreactor Synthesis of β‐Peptides

Microreactor Synthesis of β‐Peptides

Multistep Synthesis on SU-8: Combining Microfabrication and Solid-Phase Chemistry on a Single Material

Fluorous Chemistry for Synthesis and Purification of Biomolecules: Peptides, Oligosaccharides, Glycopeptides, and Oligonucleotides

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