Preparation and use of the 4-[1-[N-(9-fluorenylmethyloxycarbonyl)amino]-2-(trimethylsilyl)ethyl]phenoxyacetic acid linkage agent for solid-phase synthesis of C-terminal peptide amides: improved yields of tryptophan-containing peptides

Chao, Hann Guang; Bernatowicz, Michael S.; Matsueda, Gary R.

doi:10.1021/jo00061a049

Cited by 26 publications

(15 citation statements)

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“…Although TBAF and BTAF are the most powerful fluoride sources, their use is mandatory to cleave specific handles and protecting groups [15,16]. Furthermore, the addition of 18-crown-6/KF in DMF at 25 °C can be applied to selectively remove the Fmoc group in 70-100% yield, without provoking 03-rearrangement in Gluand Asp-containing peptides as reported by Joulli6 et al [20].…”

Section: Discussionmentioning

confidence: 95%

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Rearrangement of Glu(OtBu)- and Asp(OtBu)-containing peptides upon fluoride treatment in solid-phase synthesis

Kates

Alberício

1995

Lett Pept Sci

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Although fluoride-labile protecting groups and linkers have been developed in solid-phase peptide synthesis to add an extra level of orthogonality, fluoride ions were found to convert ~x-peptides to their corresponding ~/-or 13-peptides in Glu(OtBu)-and Asp(OtBu)-containing peptidyl resins. Different peptide sequences and fluoride reagents were examined to determine the scope of this side reaction. CZE analysis was found to be a useful analytical technique to characterize peptides with respect to this phenomenon.

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Section: Discussionmentioning

confidence: 95%

“…Recently, 4-[1-[N-(9-fluorenylmethyloxycarbonyl)amino]-2-(trimethylsilyl)ethyl]-phenoxyacetic acid and 4-[1-hydroxy-2-(trimethylsilyl)ethyl]benzoic acid were introduced to prepare C-terminal amides and acids, respectively [15,16]. Peptides could be obtained either by treatment with TFA solutions or by fluoride ions.…”

Section: Introductionmentioning

confidence: 99%

Rearrangement of Glu(OtBu)- and Asp(OtBu)-containing peptides upon fluoride treatment in solid-phase synthesis

Kates

Alberício

1995

Lett Pept Sci

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“…Peptidyl-resin was deprotected and cleaved by treatment with HF containing appropriate scavengers. Peptides were purified to homogeneity by reverse-phase HPLC (Chao et al, 1993) and their identity was established by amino acid analysis (Liu & Boykins, 1989) and electrospray or fast atom bombardment mass spectrometry analysis.…”

Section: Peptide Synthesis and Purificationmentioning

confidence: 99%

Characterization of a new four‐chain coiled‐coil: Influence of chain length on stability

et al. 1995

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Limited information is available on inherent stabilities of four-chain coiled-coils. We have developed a model system to study this folding motif using synthetic peptides derived from sequences contained in the tetramerization domain of Lac repressor. These peptides are tetrameric as judged by both gel filtration and sedimentation equilibrium and the tetramers are fully helical as determined by CD. The four-chain coiled-coils are well folded as judged by the cooperativity of thermal unfolding and by the extent of dispersion in aliphatic chemical shifts seen in NMR spectra. In addition, we measured the chain length dependence of this four-chain coiled-coil. To this end, we developed a general procedure for nonlinear curve fitting of denaturation data in oligomeric systems. The dissociation constants for bundles that contain a-helical chains 21, 28, and 35 amino acids in length are 3.1 x 6.7 X and 1.0 x M3, respectively. This corresponds to tetramer stabilities (in terms of the peptide monomer concentration) of 180 pM, 51 nM, and 280 f M , respectively. Finally, we discuss the rules governing coiledcoil formation in light of the work presented here.

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“…Removal of the N-terminal Fmoc group (deprotection) was performed using a 20% (v/v) solution of piperidine in DMF. The Fmoc deprotection step was carefully monitored by UV absorption spectroscopy at 301 nm (21) and, when necessary, suitably elongated until a baseline optical absorbance was obtained.…”

Section: Synthesis Of Derivative 1 (Dmgsck{n E -Ta1[1-14]}aca)mentioning

confidence: 99%

Solid‐phase Synthesis of a Peptide Derivative of Thymosin alpha1 and Initial Studies on its ^99mTc‐Radiolabelling

Klimentzou

Beck²,

Varvarigou

et al. 2007

Chem Biol Drug Des

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A derivative (1) of the immunopotentiating 28-peptide thymosin alpha1 has been especially designed, so that it can be (99m)Tc-radiolabelled, and synthesized following the Fmoc solid-phase peptide synthesis approach. Derivative 1 contains the N-terminal fragment Talpha1[1-14] as a bioactive segment, at the C-terminus of which a (99m)Tc-chelating moiety consisting of N(alpha),N(alpha)-dimethylglycine, serine and cysteine is linked through the N(epsilon)-amino group of a 'bifunctional' lysine residue; the latter is indirectly anchored on the solid-phase peptide synthesis resin through 6-aminocaproic acid (dmGSCK{N(epsilon)-Talpha1[1-14]}Aca). Synthetic derivative 1 was obtained at high overall yield (approximately 35%) and purity (>95%) and shown to be efficiently radiolabelled with (99m)Tc, thus resulting in the first, to our knowledge, so far reported (99m)Tc-radiolabelled derivative of thymosin alpha1, which may be eventually used as a specific molecular tool for the in vitro/in vivo study of the mode of action of the parent bioactive peptide.

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Preparation and use of the 4-[1-[N-(9-fluorenylmethyloxycarbonyl)amino]-2-(trimethylsilyl)ethyl]phenoxyacetic acid linkage agent for solid-phase synthesis of C-terminal peptide amides: improved yields of tryptophan-containing peptides

Cited by 26 publications

References 0 publications

Rearrangement of Glu(OtBu)- and Asp(OtBu)-containing peptides upon fluoride treatment in solid-phase synthesis

Rearrangement of Glu(OtBu)- and Asp(OtBu)-containing peptides upon fluoride treatment in solid-phase synthesis

Characterization of a new four‐chain coiled‐coil: Influence of chain length on stability

Solid‐phase Synthesis of a Peptide Derivative of Thymosin alpha1 and Initial Studies on its ^99mTc‐Radiolabelling

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Preparation and use of the 4-[1-[N-(9-fluorenylmethyloxycarbonyl)amino]-2-(trimethylsilyl)ethyl]phenoxyacetic acid linkage agent for solid-phase synthesis of C-terminal peptide amides: improved yields of tryptophan-containing peptides

Cited by 26 publications

References 0 publications

Rearrangement of Glu(OtBu)- and Asp(OtBu)-containing peptides upon fluoride treatment in solid-phase synthesis

Rearrangement of Glu(OtBu)- and Asp(OtBu)-containing peptides upon fluoride treatment in solid-phase synthesis

Characterization of a new four‐chain coiled‐coil: Influence of chain length on stability

Solid‐phase Synthesis of a Peptide Derivative of Thymosin alpha1 and Initial Studies on its 99mTc‐Radiolabelling

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Product

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Solid‐phase Synthesis of a Peptide Derivative of Thymosin alpha1 and Initial Studies on its ^99mTc‐Radiolabelling