N,<i>O</i>‐bisFmoc derivatives of <i>N</i>‐(2‐hydroxy‐4‐methoxybenzyl)‐amino acids: Useful intermediates in peptide synthesis

Johnson, Tony; Quibell, Martin; Sheppard, R. C.

doi:10.1002/psc.310010104

Cited by 95 publications

(80 citation statements)

References 23 publications

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“…Hundreds of cartridges Furthermore, two special Fmoc-protected alanines, could be run at the same time using commercial 24-hole whose amide was protected with a hydroxymethoxy-vacuum lines adapted for Sep-Pak Vac C 18 cartridges. benzyl group, were used in positions 74 and 82 in order These cartridges were previously equilibrated with to reduce peptide chain agregation during peptide syn-10 ml of a solution of 65% MeOH in H 2 O (v/v) conthesis (22). This synthesis was performed on a 50 mmol taining 0.1% TFA (v/v) (solution B).…”

Section: Methodsmentioning

confidence: 99%

A Sensitive and Rapid Fluorescence-Based Assay for Determination of Tetanus Toxin Peptidase Activity

Soleilhac

Cornille

Martin

et al. 1996

Analytical Biochemistry

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Section: Methodsmentioning

confidence: 99%

A Sensitive and Rapid Fluorescence-Based Assay for Determination of Tetanus Toxin Peptidase Activity

Soleilhac

Cornille

Martin

et al. 1996

Analytical Biochemistry

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“…The use of S-Trt protection was chosen to allow acquisition of the peptide in the fully S-reduced form following cleavage and deprotection and prior to folding and oxidation. Possible base-mediated aspartimide formation of the single Asp-Gly within the peptide sequence was prevented by the use of the N-(2-hydroxy-4-methoxybenzyl) (Hmb) function [10,19]. Following cleavage and deprotection, the crude S-reduced peptide was observed by RP-HPLC to be of good purity (data not shown).…”

Section: Resultsmentioning

confidence: 91%

“…Side chain protection was afforded by tert-butyl esters and ethers for Asp, Glu, Ser and Tyr, trityl for His, Asn and Cys, 2,2,5,7,8-pentamethylchromane-6-sulfonyl for Arg and tert-butoxycarbonyl for Lys and Trp. Glycine-17 was introduced as its bis-Fmoc(2-hydroxy-4-methoxybenzyl[Hmb]) pentafluorophenyl (OPfp) ester derivative [10]. The following residue, Asp 16 , was double-coupled as its pentafluorophenyl ester for 0.5 h each time.…”

Section: Solid Phase Peptide Synthesismentioning

confidence: 99%

Chemical synthesis, characterization and activity of RK-1, a novel ?-defensin-related peptide

et al. 2000

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The 32-residue peptide, RK-1, a novel kidney-derived three disulfide-bonded member of the antimicrobial alpha-defensin family, was synthesized by the continuous flow Fmoc-solid phase method. The crude, cleaved and S-reduced linear peptide was both efficiently folded and oxidized in an acidic solution of aqueous dimethyl sulfoxide. Following purification of the resulting product, it was shown by a variety of analytical techniques, including matrix assisted laser desorption time of flight mass spectrometry, to possess a very high degree of purity. The disulfide bond pairing of the synthetic peptide was determined by 1H-NMR spectroscopy and confirmed to be a Cys1-Cys6, Cys2-Cys4, Cys3-Cys5 arrangement similar to other mammalian alpha-defensin peptides. The synthetic RK-1 was also shown to inhibit the growth of Escherichia coli type strain NCTC 10418.

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“…A synthesis in which the base labile Asp-Gly bond was protected by the incorporation of N,O-BisFmocHmb-Gly-OPfp was also performed [13]. The peptide -resin samples were treated with either 1% DBU/DMF (v/v) or 1% DBU/1% HOBt/DMF (v/w/v) for 24 h, as shown in Table 1, washed with DMF, methanol and Et 2 O and dried in vacuo.…”

Section: Aspartimide Formation Studymentioning

confidence: 99%

Peptide thioester preparation by Fmoc solid phase peptide synthesis for use in native chemical ligation

2000

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Established methodology for the preparation of peptide thioesters requires the use of t-butoxycarbonyl chemistry owing to the lability of thioester linkers to the nucleophilic reagents used in Fmoc solid phase peptide synthesis. Both the greater ease of use and the broad applicability of the method has led to the development of an Fmoc-based methodology for direct peptide thioester synthesis. It was found that successful preparation of a peptide thioester could be achieved when the non-nucleophilic base, 1,8-diazabicyclo[5.4.0]undec-7-ene, together with 1-hydroxybenzotriazole in dimethylformamide, were used as the N(alpha)-Fmoc deprotection reagent. Native chemical ligation of the resulting thioester product to an N-terminal cysteine-containing peptide was successfully performed in aqueous solution to produce a fragment peptide of human alpha-synuclein. The formation of aspartimide (cyclic imide) in a base-sensitive hexapeptide fragment of scorpion toxin II was found to be significant under the deprotection conditions used. However, this could be controlled by the judicious protection of sensitive residues using the 2-hydroxy-4-methoxybenzyl group.

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N,O‐bisFmoc derivatives of N‐(2‐hydroxy‐4‐methoxybenzyl)‐amino acids: Useful intermediates in peptide synthesis

Abstract: 2-Hydroxy-4-methoxybenzyl-amino acid residues inhibit interchain association in solid phase peptide synthesis. They are easily introduced through their N,O-bisFmoc derivatives. Preparation of a range of these derivatives is described.

Cited by 95 publications

References 23 publications

A Sensitive and Rapid Fluorescence-Based Assay for Determination of Tetanus Toxin Peptidase Activity

A Sensitive and Rapid Fluorescence-Based Assay for Determination of Tetanus Toxin Peptidase Activity

Chemical synthesis, characterization and activity of RK-1, a novel ?-defensin-related peptide

Peptide thioester preparation by Fmoc solid phase peptide synthesis for use in native chemical ligation

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