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1994•Journal of the Chemical Society Perkin Transactions 1Requires access

Amino acids and peptides. Part 38. Development of a new amino-protecting group, 2-adamantyloxycarbonyl, and its application to peptide synthesis

Yasuhiro Nishiyama, Noriyuki Shintomi, Yukihiro Kondo, Yoshio Okada

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Abstract

A new ε-amino protecting group, 2-adamantyloxycarbonyl (2-Adoc), was developed, and its application to the solid-phase synthesis of protected peptides was demonstrated in combination with Nα-fluoren-9-ylmethoxycarbonyl (Fmoc) protection and trifluoroacetic acid (TFA)-cleavable resin support. The 2-Adoc group was applied successfully also to the solution-phase peptide synthesis depending on tert-butoxycarbonyl (Boc)-chemistry.

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What this paper is about

A new ε-amino protecting group, 2-adamantyloxycarbonyl (2-Adoc), was developed, and its application to the solid-phase synthesis of protected peptides was demonstrated in combination with Nα-fluoren-9-ylmethoxycarbonyl (Fmoc) protection and trifluoroacetic acid (TFA)-cleavable resin support. The 2-Adoc group was applied successfully also to the solution-phase peptide synthesis depending on tert-butoxycarbonyl (Boc)-chemistry.

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OpenAlex reports 7 citations for this work. Citation counts describe recorded attention and do not establish research quality.

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Available abstract

A new ε-amino protecting group, 2-adamantyloxycarbonyl (2-Adoc), was developed, and its application to the solid-phase synthesis of protected peptides was demonstrated in combination with Nα-fluoren-9-ylmethoxycarbonyl (Fmoc) protection and trifluoroacetic acid (TFA)-cleavable resin support. The 2-Adoc group was applied successfully also to the solution-phase peptide synthesis depending on tert-butoxycarbonyl (Boc)-chemistry.

Key concepts: Trifluoroacetic acid, Protecting group, Chemistry, Peptide synthesis, Peptide, Amino acid, Solid-phase synthesis, Group (periodic table)

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