| Автор | Nishiyama, Yasuhiro |
| Автор | Shikama, Suguru |
| Автор | Morita, Ken-ichi |
| Автор | Kurita, Keisuke |
| Дата выпуска | 2000 |
| dc.description | A new hydroxy-protecting group for Ser and Thr, cyclohexyl (Chx), has been developed, and its application to peptide synthesis is described. The Chx group is introduced to the hydroxy functions of Boc-Ser-OH and Boc-Thr-OH in two steps; Boc-Ser-OH and Boc-Thr-OH are treated with NaH and then allowed to react with 3-bromocyclohexene to afford N-Boc-O-(cyclohex-2-enyl)-Ser and N-Boc-O-(cyclohex-2-enyl)-Thr in satisfactory yields, which are hydrogenated in the presence of PtO2 to give Boc-Ser(Chx)-OH and Boc-Thr(Chx)-OH in good yields. The O-Chx group is stable to various acidic and basic conditions including TFA and 20% piperidine in DMF. It is not removed with catalytic hydrogenation over Pdâ charcoal. The Chx group is, however, removed quantitatively with 1 mol dm<sup>â 3</sup> trifluoromethanesulfonic acidâ thioanisole in TFA over a short period. These results indicate that the Chx group is suitable for the hydroxy-protection of Ser and Thr in peptide synthesis based on Boc-chemistry and can be used also in combination with either N<sup>α</sup>-Fmoc or N<sup>α</sup>-Z-protection. The apparent rate constant for removal of the Chx group with 50% TFA in CH2Cl2 (kChx) is found to be less than a twentieth of that of the Bzl group (kBzl), confirming the substantial stability of the Chx group under common Boc-deprotection conditions. Simulations of solid-phase peptide syntheses using kChx and kBzl indicate that the Chx group would be adequate for solid-phase synthesis of large peptides and proteins. Solid-phase synthesis of a peptide and conventional solution synthesis of a protected peptide segment using Chx protection are also demonstrated. |
| Формат | application.pdf |
| Издатель | Royal Society of Chemistry |
| Название | Cyclohexyl ether as a new hydroxy-protecting group for serine and threonine in peptide synthesisâ Amino acids used in this study are of l-configuration. Abbreviations used in this report for amino acids, peptides, and their derivatives are those recommended by the IUPACâ IUB Joint Commission on Biochemical Nomenclature: Biochem. J., 1984, 219, 345; Eur. J. Biochem., 1984, 138, 9; Pure Appl. Chem., 1984, 56, 595.1 |
| Тип | ART |
| Журнал | Journal of the Chemical Society, Perkin Transactions 1 |
| Первая страница | 1949 |
| Последняя страница | 1954 |
| Аффилиация | Nishiyama Yasuhiro; Department of Industrial Chemistry, Faculty of Engineering, Seikei University, Musashino-shi |
| Аффилиация | Shikama Suguru; Department of Industrial Chemistry, Faculty of Engineering, Seikei University, Musashino-shi |
| Аффилиация | Morita Ken-ichi; Department of Industrial Chemistry, Faculty of Engineering, Seikei University, Musashino-shi |
| Аффилиация | Kurita Keisuke; Department of Industrial Chemistry, Faculty of Engineering, Seikei University, Musashino-shi |
| Выпуск | 12 |
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