ISOPENICILLIN-N SYNTHASE - A NEW MODE OF REACTIVITY
Incubation of L-δ-(α-aminoadipoyl)-L-(3,3-difluorohomocysteinyl)-D-valine [an analogue of the natural substrate: L-δ-(α-aminoadipoyl)-L-(cysteinyl)-D-valine] with isopenicillin N synthase (IPNS) resulted in the production of a thiocarboxylic acid, i.e. both equivalents of the dioxygen cosubstrate we...
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| Format: | Journal article |
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1992
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| _version_ | 1797078952615870464 |
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| author | Baldwin, J Lynch, G Schofield, C |
| author_facet | Baldwin, J Lynch, G Schofield, C |
| author_sort | Baldwin, J |
| collection | OXFORD |
| description | Incubation of L-δ-(α-aminoadipoyl)-L-(3,3-difluorohomocysteinyl)-D-valine [an analogue of the natural substrate: L-δ-(α-aminoadipoyl)-L-(cysteinyl)-D-valine] with isopenicillin N synthase (IPNS) resulted in the production of a thiocarboxylic acid, i.e. both equivalents of the dioxygen cosubstrate were utilised to oxidise a single carbon of the cysteinyl analogue. This result and others are rationalised in terms of mechanistic proposals for the first ring closure by IPNS. The synthesis of L-difluorohomocysteine and related structures, via 3,3-difluoro-β-lactams, is described. © 1992. |
| first_indexed | 2024-03-07T00:38:47Z |
| format | Journal article |
| id | oxford-uuid:825311f1-8daf-4787-84b3-32d107ffbbb3 |
| institution | University of Oxford |
| last_indexed | 2024-03-07T00:38:47Z |
| publishDate | 1992 |
| record_format | dspace |
| spelling | oxford-uuid:825311f1-8daf-4787-84b3-32d107ffbbb32022-03-26T21:36:33ZISOPENICILLIN-N SYNTHASE - A NEW MODE OF REACTIVITYJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:825311f1-8daf-4787-84b3-32d107ffbbb3Symplectic Elements at Oxford1992Baldwin, JLynch, GSchofield, CIncubation of L-δ-(α-aminoadipoyl)-L-(3,3-difluorohomocysteinyl)-D-valine [an analogue of the natural substrate: L-δ-(α-aminoadipoyl)-L-(cysteinyl)-D-valine] with isopenicillin N synthase (IPNS) resulted in the production of a thiocarboxylic acid, i.e. both equivalents of the dioxygen cosubstrate were utilised to oxidise a single carbon of the cysteinyl analogue. This result and others are rationalised in terms of mechanistic proposals for the first ring closure by IPNS. The synthesis of L-difluorohomocysteine and related structures, via 3,3-difluoro-β-lactams, is described. © 1992. |
| spellingShingle | Baldwin, J Lynch, G Schofield, C ISOPENICILLIN-N SYNTHASE - A NEW MODE OF REACTIVITY |
| title | ISOPENICILLIN-N SYNTHASE - A NEW MODE OF REACTIVITY |
| title_full | ISOPENICILLIN-N SYNTHASE - A NEW MODE OF REACTIVITY |
| title_fullStr | ISOPENICILLIN-N SYNTHASE - A NEW MODE OF REACTIVITY |
| title_full_unstemmed | ISOPENICILLIN-N SYNTHASE - A NEW MODE OF REACTIVITY |
| title_short | ISOPENICILLIN-N SYNTHASE - A NEW MODE OF REACTIVITY |
| title_sort | isopenicillin n synthase a new mode of reactivity |
| work_keys_str_mv | AT baldwinj isopenicillinnsynthaseanewmodeofreactivity AT lynchg isopenicillinnsynthaseanewmodeofreactivity AT schofieldc isopenicillinnsynthaseanewmodeofreactivity |