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1986•Chemical and Pharmaceutical BulletinOpen access

Studies on peptides. CXXXIV. Evaluation of S-1-adamantylcysteine for peptide synthesis.

Nobutaka Fujii, Akira Otaka, Susumu Funakoshi, Haruaki Yajima, Osamu Nishimura, Masahiko Fujino

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Abstract

The S-1-adamantyl (Ad) group of cysteine is more stable to TFA treatment than the S-p-methoxybenzyl (MBzl) group, but is cleavable by 1 M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid at 0°C within 60 min or by (CF3COO)3 Tl under similar conditions. S-Ad-cysteine is less susceptible to sulfoxide formation than the S-MBzl group. Trimethylphenyl-thiosilane is an effective reducing reagent of the sulfoxide.

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The S-1-adamantyl (Ad) group of cysteine is more stable to TFA treatment than the S-p-methoxybenzyl (MBzl) group, but is cleavable by 1 M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid at 0°C within 60 min or by (CF3COO)3 Tl under similar conditions. S-Ad-cysteine is less susceptible to sulfoxide formation than the S-MBzl group. Trimethylphenyl-thiosilane is an effective reducing reagent of the sulfoxide.

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Available abstract

The S-1-adamantyl (Ad) group of cysteine is more stable to TFA treatment than the S-p-methoxybenzyl (MBzl) group, but is cleavable by 1 M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid at 0°C within 60 min or by (CF3COO)3 Tl under similar conditions. S-Ad-cysteine is less susceptible to sulfoxide formation than the S-MBzl group. Trimethylphenyl-thiosilane is an effective reducing reagent of the sulfoxide.

Key concepts: Thioanisole, Chemistry, Trifluoroacetic acid, Sulfoxide, Cysteine, Reagent, Peptide, Protecting group

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