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

Min Cheng Chien; Yi Kai Lin; Yong Liao; Szu Hsuan Chen; Yen Wei Chen; Chien Yu Liang; Vijayasimha Molakaseema; Sodio C.N. Hsu; Chun Cheng Lin; Hui Ting Chen; Chai Lin Kao

doi:10.1021/acsomega.3c06640

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

Min Cheng Chien, Yi Kai Lin, Yong Liao, Szu Hsuan Chen, Yen Wei Chen, Chien Yu Liang, Vijayasimha Molakaseema, Sodio C.N. Hsu, Chun Cheng Lin, Hui Ting Chen^*, Chai Lin Kao^*

^*Corresponding author for this work

Faculty of Pharmacy

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	41855-41864
Number of pages	10
Journal	ACS Omega
Volume	8
Issue number	44
DOIs	https://doi.org/10.1021/acsomega.3c06640
State	Published - 7 Nov 2023

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@article{36b52285aca34d50b33be65afb111498,

title = "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.",

author = "Chien, {Min Cheng} and Lin, {Yi Kai} and Yong Liao and Chen, {Szu Hsuan} and Chen, {Yen Wei} and Liang, {Chien Yu} and Vijayasimha Molakaseema and Hsu, {Sodio C.N.} and Lin, {Chun Cheng} and Chen, {Hui Ting} and Kao, {Chai Lin}",

note = "Publisher Copyright: {\textcopyright} 2023 The Authors. Published by American Chemical Society.",

year = "2023",

month = nov,

day = "7",

doi = "10.1021/acsomega.3c06640",

language = "English",

volume = "8",

pages = "41855--41864",

journal = "ACS Omega",

issn = "2470-1343",

publisher = "American Chemical Society",

number = "44",

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TY - JOUR

T1 - One-Step Synthesis of 3-(Fmoc-amino acid)-3,4-diaminobenzoic Acids

AU - Chien, Min Cheng

AU - Lin, Yi Kai

AU - Liao, Yong

AU - Chen, Szu Hsuan

AU - Chen, Yen Wei

AU - Liang, Chien Yu

AU - Molakaseema, Vijayasimha

AU - Hsu, Sodio C.N.

AU - Lin, Chun Cheng

AU - Chen, Hui Ting

AU - Kao, Chai Lin

PY - 2023/11/7

Y1 - 2023/11/7

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=85178064053&partnerID=8YFLogxK

U2 - 10.1021/acsomega.3c06640

DO - 10.1021/acsomega.3c06640

M3 - Article

AN - SCOPUS:85178064053

SN - 2470-1343

VL - 8

SP - 41855

EP - 41864

JO - ACS Omega

JF - ACS Omega

IS - 44

ER -

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

Abstract

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