Facile Synthesis of N-(9-Fluorenylmethyloxycarbonyl)-3-amino-3-(4,5-dimethoxy-2-nitrophenyl)propionic Acid as a Photocleavable Linker for Solid-Phase Peptide Synthesis

Jaehi Kim; San Kyeong; Dong-Sik Shin; Sewon Yeo; Joonhyuk Yim; Yoon-Sik Lee

doi:10.1055/s-0032-1318314

Synlett, Table of Contents

Synlett 2013; 24(6): 733-736
DOI: 10.1055/s-0032-1318314

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Facile Synthesis of N-(9-Fluorenylmethyloxycarbonyl)-3-amino-3-(4,5-dimethoxy-2-nitrophenyl)propionic Acid as a Photocleavable Linker for Solid-Phase Peptide Synthesis

Jaehi Kim*

School of Chemical and Biological Engineering, Seoul National University, Gwanak-Gu, Seoul 151-744, Korea Fax: +82(2)8769625 Email: yslee@snu.ac.kr

,

San Kyeong

School of Chemical and Biological Engineering, Seoul National University, Gwanak-Gu, Seoul 151-744, Korea Fax: +82(2)8769625 Email: yslee@snu.ac.kr

,

Dong-Sik Shin

School of Chemical and Biological Engineering, Seoul National University, Gwanak-Gu, Seoul 151-744, Korea Fax: +82(2)8769625 Email: yslee@snu.ac.kr

,

Sewon Yeo

School of Chemical and Biological Engineering, Seoul National University, Gwanak-Gu, Seoul 151-744, Korea Fax: +82(2)8769625 Email: yslee@snu.ac.kr

,

Joonhyuk Yim

School of Chemical and Biological Engineering, Seoul National University, Gwanak-Gu, Seoul 151-744, Korea Fax: +82(2)8769625 Email: yslee@snu.ac.kr

,

Yoon-Sik Lee

School of Chemical and Biological Engineering, Seoul National University, Gwanak-Gu, Seoul 151-744, Korea Fax: +82(2)8769625 Email: yslee@snu.ac.kr

› Author Affiliations

Abstract

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Abstract

A photocleavable linker, N-(9-fluorenylmethyloxycarbonyl)-3-amino-3-(4,5-dimethoxy-2-nitrophenyl)propionic acid was synthesized from veratraldehyde, with simple reaction and separation steps. This linker was stable under the normal solid-phase peptide synthesis conditions and rearranged to a labile form when irradiated with UV light (λ = 365 nm). A model peptide sequence (YGGFL) was synthesized and released from solid supports with high efficiency by UV irradiation.

Key words

photochemistry - photocleavable linker - solid-phase synthesis - amino acid derivative - peptides

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References

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