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One-Step Synthesis of 3-(Fmoc-amino acid)-3,4-diaminobenzoic Acids.

ABSTRACT: A one-step method for synthesizing 3-(Fmoc-amino acid)-3,4-diaminobenzoic acids was used to prepare preloaded diaminobenzoate resin. The coupling of free diaminobenzoic acid and Fmoc-amino acids gave pure products in 40-94% yield without any purification step in addition to precipitation except for histidine. For the proline residue, crude products were collected and used for solid-phase peptide synthesis to give a moderate yield of a pentapeptide. In addition, this method was used to prepare unusual amino acid derivatives, namely, (2-naphthyl) alanine and 6-aminohexanoic acid derivatives, in 50 and 65% yield, respectively.

SUBMITTER: Chien MC

PROVIDER: S-EPMC10634083 | biostudies-literature | 2023 Nov

REPOSITORIES: biostudies-literature

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One-Step Synthesis of 3-(Fmoc-amino acid)-3,4-diaminobenzoic Acids.

Chien Min-Cheng MC Lin Yi Kai YK Liao Yong Y Chen Szu-Hsuan SH Chen Yen-Wei YW Liang Chien-Yu CY Molakaseema Vijayasimha V Hsu Sodio C N SCN Lin Chun-Cheng CC Chen Hui-Ting HT Kao Chai-Lin CL

ACS omega 20231024 44

A one-step method for synthesizing 3-(Fmoc-amino acid)-3,4-diaminobenzoic acids was used to prepare preloaded diaminobenzoate resin. The coupling of free diaminobenzoic acid and Fmoc-amino acids gave pure products in 40-94% yield without any purification step in addition to precipitation except for histidine. For the proline residue, crude products were collected and used for solid-phase peptide synthesis to give a moderate yield of a pentapeptide. In addition, this method was used to prepare un ...[more]

PMID: 37970022

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