1988Journal of the Chemical Society Chemical CommunicationsRequires access

A modified benzhydrylamine as a handle reagent for the solid phase synthesis of peptide amides based on the fluorenylmethoxycarbonyl method

Susumu Funakoshi, Eigoro Murayama, Lili Guo, Nobutaka Fujii, Haruaki Yajima

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Abstract

An easily preparable dimethoxybenzhydrylamine derivative, 3-(α-Fmoc-amino-4-methoxybenzyl)-4-methoxyphenyl propionic acid (Fmoc = fluoren-9-ylmethoxycarbonyl) is a useful precursor of the C-terminal amide, when applied to Fmoc-based solid phase peptide synthesis; as a cleavage reagent from the resin, thioanisole-mediated trimethylsilyl bromide in trifluoroacetic acid is recommended.

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An easily preparable dimethoxybenzhydrylamine derivative, 3-(α-Fmoc-amino-4-methoxybenzyl)-4-methoxyphenyl propionic acid (Fmoc = fluoren-9-ylmethoxycarbonyl) is a useful precursor of the C-terminal amide, when applied to Fmoc-based solid phase peptide synthesis; as a cleavage reagent from the resin, thioanisole-mediated trimethylsilyl bromide in trifluoroacetic acid is recommended.

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Available abstract

An easily preparable dimethoxybenzhydrylamine derivative, 3-(α-Fmoc-amino-4-methoxybenzyl)-4-methoxyphenyl propionic acid (Fmoc = fluoren-9-ylmethoxycarbonyl) is a useful precursor of the C-terminal amide, when applied to Fmoc-based solid phase peptide synthesis; as a cleavage reagent from the resin, thioanisole-mediated trimethylsilyl bromide in trifluoroacetic acid is recommended.

Key concepts: Trifluoroacetic acid, Reagent, Chemistry, Thioanisole, Peptide synthesis, Solid-phase synthesis, Combinatorial chemistry, Peptide

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