A carbene-yielding amino acid for incorporation into peptide photoaffinity reagents.
3-[p-[3-(Trifluoromethyl)-3H-diazirin-3-yl]phenyl]alanine has been prepared in 10 steps from p-bromobenzyl alcohol. The alcohol was converted to 3-(alpha-iodo-p-tolyl)-3-(trifluoromethyl)-3H-diazirine, which was used to alkylate N-(diphenylmethylene)glycine ethyl ester. After deprotection the amino...
| Main Authors: | , |
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| Format: | Journal article |
| Language: | English |
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1985
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| _version_ | 1797106374950256640 |
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| author | Shih, L Bayley, H |
| author_facet | Shih, L Bayley, H |
| author_sort | Shih, L |
| collection | OXFORD |
| description | 3-[p-[3-(Trifluoromethyl)-3H-diazirin-3-yl]phenyl]alanine has been prepared in 10 steps from p-bromobenzyl alcohol. The alcohol was converted to 3-(alpha-iodo-p-tolyl)-3-(trifluoromethyl)-3H-diazirine, which was used to alkylate N-(diphenylmethylene)glycine ethyl ester. After deprotection the amino acid was obtained with an overall yield of 18%. The D- and L-isomers of 3-[p-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenyl]alanine have also been resolved, and 3-[p-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenyl]alanine labeled with tritium has been prepared. The advantages of using this amino acid as a building block for peptide photoaffinity reagents is discussed. |
| first_indexed | 2024-03-07T07:00:43Z |
| format | Journal article |
| id | oxford-uuid:ffa6bed2-f7b2-48de-b438-7459c4f90ac5 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T07:00:43Z |
| publishDate | 1985 |
| record_format | dspace |
| spelling | oxford-uuid:ffa6bed2-f7b2-48de-b438-7459c4f90ac52022-03-27T13:46:32ZA carbene-yielding amino acid for incorporation into peptide photoaffinity reagents.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:ffa6bed2-f7b2-48de-b438-7459c4f90ac5EnglishSymplectic Elements at Oxford1985Shih, LBayley, H3-[p-[3-(Trifluoromethyl)-3H-diazirin-3-yl]phenyl]alanine has been prepared in 10 steps from p-bromobenzyl alcohol. The alcohol was converted to 3-(alpha-iodo-p-tolyl)-3-(trifluoromethyl)-3H-diazirine, which was used to alkylate N-(diphenylmethylene)glycine ethyl ester. After deprotection the amino acid was obtained with an overall yield of 18%. The D- and L-isomers of 3-[p-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenyl]alanine have also been resolved, and 3-[p-[3-(trifluoromethyl)-3H-diazirin-3-yl]phenyl]alanine labeled with tritium has been prepared. The advantages of using this amino acid as a building block for peptide photoaffinity reagents is discussed. |
| spellingShingle | Shih, L Bayley, H A carbene-yielding amino acid for incorporation into peptide photoaffinity reagents. |
| title | A carbene-yielding amino acid for incorporation into peptide photoaffinity reagents. |
| title_full | A carbene-yielding amino acid for incorporation into peptide photoaffinity reagents. |
| title_fullStr | A carbene-yielding amino acid for incorporation into peptide photoaffinity reagents. |
| title_full_unstemmed | A carbene-yielding amino acid for incorporation into peptide photoaffinity reagents. |
| title_short | A carbene-yielding amino acid for incorporation into peptide photoaffinity reagents. |
| title_sort | carbene yielding amino acid for incorporation into peptide photoaffinity reagents |
| work_keys_str_mv | AT shihl acarbeneyieldingaminoacidforincorporationintopeptidephotoaffinityreagents AT bayleyh acarbeneyieldingaminoacidforincorporationintopeptidephotoaffinityreagents AT shihl carbeneyieldingaminoacidforincorporationintopeptidephotoaffinityreagents AT bayleyh carbeneyieldingaminoacidforincorporationintopeptidephotoaffinityreagents |