Gel phase 13C n.m.r. spectroscopy as an analytical method in solid (gel) phase peptide synthesis

Epton, R.; Goddard, Peter; Ivin, K. J.

doi:10.1016/0032-3861(80)90134-2

Cited by 41 publications

(18 citation statements)

References 5 publications

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“…Leu-Enkephalin has been extensively used to test the suitability of supports in SPPS, therefore providing a useful comparison with available data in the field. [25][26][27][28][29] Both SLURPS-HMPA-1.5 (18) and SLURPS-HMPA-8.5…”

Section: Spps Using Slurps Resinsmentioning

confidence: 99%

“…4,7 We decided to prepare a SLURPS-bound 4-vinyl benzoic ester 28. Wittig chemistry led from 4-bromomethyl benzoic acid to 4-vinyl benzoic acid (29) in high yields (90 %), which was converted to its methyl ester 30 as solution-phase equivalent of 28 via in situ formation of the corresponding acyl chloride and subsequent methanolysis again in high yields (93 %).…”

Section: Solid-phase Organic Synthesis Using Slurps Resinsmentioning

confidence: 99%

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Novel Non-PEG Derived Polyethers as Solid Supports. 2. Solid-Phase Synthesis Studies

et al. 2007

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Novel non-PEG derived polyether resins, coined SLURPS (Superior Liquid Uptake Resins forPolymer-supported Synthesis), were studied for their performance in solid-phase synthesis. Novel amino functional resins, SLURPS-NH 2 , were prepared with a loading of up to 8.5 mmol/g and employed successfully in the solid-phase synthesis of Leu-Enkephalin. The peptide was obtained with the same 2 purity when compared to its synthesis with commercial standard poly(dimethyl acrylamide) resins.Furthermore we show loading and cleavage of aromatic carboxylic acids in excellent yield. The advantageous solvent compatibility of our support was demonstrated through the biphasic dihydroxylation of alkenes with OsO 4 in t-BuOH/water mixtures producing bound 1,2-diols and synthesis and removal of a bound oxime using ethanol/water mixtures both in excellent yields. Reactions were easily monitored by gel-phase NMR and FTIR These results show that SLURPS are very well suited for organic transformations using highly polar solvent mixtures and reagents and this at much higher loading levels than standard amphiphilic resins of similar solvent compatibility. Graphical Abstract:O OH SLURPS

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Section: Spps Using Slurps Resinsmentioning

confidence: 99%

Section: Solid-phase Organic Synthesis Using Slurps Resinsmentioning

confidence: 99%

Novel Non-PEG Derived Polyethers as Solid Supports. 2. Solid-Phase Synthesis Studies

et al. 2007

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“…Consequently, the technique of NMR spectroscopy has also moved from solution to solid-phase and it is now possible to perform gel-phase NMR experiments [7]. Furthermore, it is currently also possible to perform magic angle spinning (MAS) experiments as well as to use MAS combined with a high-resolution-probe technology [8].…”

Section: Introductionmentioning

confidence: 99%

A Combination of Different Spectroscopic Techniques to Monitor the “in situ” Solid‐phase Synthesis of Organic Molecules

Cironi¹,

Álvarez²,

Alberício³

2004

QSAR Comb. Sci.

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The efficacy, limitations and scope of different spectroscopic techniques to monitor solid-phase syntheses are discussed. The total solid-phase synthesis of a natural product derivative, 3,17-di-O-acetyllamellarin U, has been monitored by gel-phase NMR and HR-MAS NMR as appropriate. FT-IR and colorimetric tests also proved to be valuable tools for monitoring the progress of reactions. While the data obtained by FT-IR provided valuable information on some functional groups, the NMR data provided more specific structural information that allowed the progress of reactions to be monitored. After several reaction steps the ™aging∫ of the resin only allowed the product covalently anchored to the resin to be investigated using an HR-MAS probe, a situation that severely limited the depth of analysis available.

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“…These methods include colorimetric analysis of resin-bound peptides with ninhydrin, isatin, picric acid, bromophenol blue dye and quinoline yellow dye [1], continuous conductance measurement of reaction effluents [2], spectroscopic monitoring of Fmoc chromophore in continuous-flow synthesis [3], and Edman sequencing [4]. Gel-phase NMR spectroscopy has also been employed [5]. More recently, high-resolution probe technology together with 1H NMR spectroscopy has been used to identify chemical compounds covalently bound to a single solid-phase synthesis bead [6].…”

Section: Introductionmentioning

confidence: 99%

Rapid semi-on-line monitoring of Fmoc solid-phase peptide synthesis by matrix-assisted laser desorption/ionization mass spectrometry

et al. 1997

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SUMMARYA simple yet highly effective application of matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) for the rapid monitoring of Fmoc solid-phase peptide synthesis is described. A few beads of the resin are removed at any desired step during synthesis, the fully protected peptide is cleaved from the resin and an MS spectrum of the analytes present is produced. Some standard side-chain protecting groups may be cleaved off during sample preparation for MS analysis; however, these cleavages are readily identified. Using this approach, incomplete amino acid acylations are readily detected in approximately the same time as by traditional tests such as ninhydrin. The semi-on-line method also lends itself to ready optimization of synthesis protocols and to the examination of resin-bound peptide side reactions which may not be detectable by chemical means.

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Gel phase 13C n.m.r. spectroscopy as an analytical method in solid (gel) phase peptide synthesis

Cited by 41 publications

References 5 publications

Novel Non-PEG Derived Polyethers as Solid Supports. 2. Solid-Phase Synthesis Studies

Novel Non-PEG Derived Polyethers as Solid Supports. 2. Solid-Phase Synthesis Studies

A Combination of Different Spectroscopic Techniques to Monitor the “in situ” Solid‐phase Synthesis of Organic Molecules

Rapid semi-on-line monitoring of Fmoc solid-phase peptide synthesis by matrix-assisted laser desorption/ionization mass spectrometry

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