Abstract
Peptides containing various alpha,alpha-disubstituted alpha-amino acids, such as alpha-aminoisobutyric acid (Aib), 1-aminocyclopentane-1-carboxylic acid, alpha-methylphenylalanine, and 3-amino-3,4,5,6-tetrahydro-2Hpyran-3-carboxylic acid have been synthesized from the N- to the C-terminus by the ‘azirine/oxazolone method’ under solid-phase conditions. In this convenient method for the synthesis of sterically demanding peptides on solid-phase, 2H-azirin-3-amines are used to introduce the alpha,alpha-disubstituted alpha-amino acids without the need for additional reagents. Furthermore, the synthesis of poly(Aib) sequences has been explored.
| Item Type: | Journal Article, refereed, original work |
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| Communities & Collections: | 07 Faculty of Science > Department of Chemistry |
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| Dewey Decimal Classification: | 540 Chemistry |
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| Scopus Subject Areas: | Physical Sciences > Catalysis
Life Sciences > Biochemistry
Life Sciences > Drug Discovery
Physical Sciences > Physical and Theoretical Chemistry
Physical Sciences > Organic Chemistry
Physical Sciences > Inorganic Chemistry |
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| Uncontrolled Keywords: | Physical and Theoretical Chemistry, Inorganic Chemistry, Organic Chemistry, Biochemistry, Drug Discovery, Catalysis |
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| Language: | English |
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| Date: | 2006 |
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| Deposited On: | 22 May 2012 07:18 |
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| Last Modified: | 07 Mar 2025 02:40 |
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| Publisher: | Verlag Helvetica Chimica Acta |
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| ISSN: | 0018-019X |
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| Funders: | Swiss National Science Foundation, F. Hoffmann-La Roche AG, Basel |
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| OA Status: | Green |
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| Free access at: | Publisher DOI. An embargo period may apply. |
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| Publisher DOI: | https://doi.org/10.1002/hlca.200690019 |
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| Project Information: | - Funder: SNSF
- Grant ID:
- Project Title: Swiss National Science Foundation
- Funder:
- Grant ID:
- Project Title: F. Hoffmann-La Roche AG, Basel
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Stamm, Simon