Inhibition of the alpha-L-arabinofuranosidase III of Monilinia fructigena by 1,4-dideoxy-1,4-imino-L-threitol and 1,4-dideoxy-1,4-imino-L-arabinitol.
1. 1,4-Dideoxy-1,4-imino-L-threitol was synthesized and the synthesis of 1,4-dideoxy-1,4-imino-L-arabinitol was improved. 2. Both compounds are competitive inhibitors of Monilinia fructigena alpha-L-arabinofuranosidase III, the additional hydroxymethyl group in the arabinitol contributing about 17.8...
| Main Authors: | , , , , |
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| Format: | Journal article |
| Language: | English |
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1990
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| _version_ | 1797102989683458048 |
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| author | Axamawaty, M Fleet, G Hannah, K Namgoong, S Sinnott, M |
| author_facet | Axamawaty, M Fleet, G Hannah, K Namgoong, S Sinnott, M |
| author_sort | Axamawaty, M |
| collection | OXFORD |
| description | 1. 1,4-Dideoxy-1,4-imino-L-threitol was synthesized and the synthesis of 1,4-dideoxy-1,4-imino-L-arabinitol was improved. 2. Both compounds are competitive inhibitors of Monilinia fructigena alpha-L-arabinofuranosidase III, the additional hydroxymethyl group in the arabinitol contributing about 17.8 kj/mol (4.25 kcal/mol) to the Gibbs free energy of binding. 3. The affinities (1/Ki) of both compounds vary with pH in a classical bell-shaped way, the pKa value being that of the acid-catalytic group on the enzyme [5.9; Selwood and Sinnott (1988) Biochem. J. 254, 899-901] and the pKb values being those of the free inhibitors, 7.6 and 7.8 respectively. 4. On the basis of these and literature data we suggest that efficient inhibition of a glycosidase at its pH optimum by an appropriate iminoalditol will be found when the pKa of the iminoalditol is below that of the acid-catalytic group of the target enzyme. |
| first_indexed | 2024-03-07T06:13:39Z |
| format | Journal article |
| id | oxford-uuid:f060c789-6682-4bd6-9dc1-b21bb61f87bc |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-07T06:13:39Z |
| publishDate | 1990 |
| record_format | dspace |
| spelling | oxford-uuid:f060c789-6682-4bd6-9dc1-b21bb61f87bc2022-03-27T11:47:22ZInhibition of the alpha-L-arabinofuranosidase III of Monilinia fructigena by 1,4-dideoxy-1,4-imino-L-threitol and 1,4-dideoxy-1,4-imino-L-arabinitol.Journal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:f060c789-6682-4bd6-9dc1-b21bb61f87bcEnglishSymplectic Elements at Oxford1990Axamawaty, MFleet, GHannah, KNamgoong, SSinnott, M1. 1,4-Dideoxy-1,4-imino-L-threitol was synthesized and the synthesis of 1,4-dideoxy-1,4-imino-L-arabinitol was improved. 2. Both compounds are competitive inhibitors of Monilinia fructigena alpha-L-arabinofuranosidase III, the additional hydroxymethyl group in the arabinitol contributing about 17.8 kj/mol (4.25 kcal/mol) to the Gibbs free energy of binding. 3. The affinities (1/Ki) of both compounds vary with pH in a classical bell-shaped way, the pKa value being that of the acid-catalytic group on the enzyme [5.9; Selwood and Sinnott (1988) Biochem. J. 254, 899-901] and the pKb values being those of the free inhibitors, 7.6 and 7.8 respectively. 4. On the basis of these and literature data we suggest that efficient inhibition of a glycosidase at its pH optimum by an appropriate iminoalditol will be found when the pKa of the iminoalditol is below that of the acid-catalytic group of the target enzyme. |
| spellingShingle | Axamawaty, M Fleet, G Hannah, K Namgoong, S Sinnott, M Inhibition of the alpha-L-arabinofuranosidase III of Monilinia fructigena by 1,4-dideoxy-1,4-imino-L-threitol and 1,4-dideoxy-1,4-imino-L-arabinitol. |
| title | Inhibition of the alpha-L-arabinofuranosidase III of Monilinia fructigena by 1,4-dideoxy-1,4-imino-L-threitol and 1,4-dideoxy-1,4-imino-L-arabinitol. |
| title_full | Inhibition of the alpha-L-arabinofuranosidase III of Monilinia fructigena by 1,4-dideoxy-1,4-imino-L-threitol and 1,4-dideoxy-1,4-imino-L-arabinitol. |
| title_fullStr | Inhibition of the alpha-L-arabinofuranosidase III of Monilinia fructigena by 1,4-dideoxy-1,4-imino-L-threitol and 1,4-dideoxy-1,4-imino-L-arabinitol. |
| title_full_unstemmed | Inhibition of the alpha-L-arabinofuranosidase III of Monilinia fructigena by 1,4-dideoxy-1,4-imino-L-threitol and 1,4-dideoxy-1,4-imino-L-arabinitol. |
| title_short | Inhibition of the alpha-L-arabinofuranosidase III of Monilinia fructigena by 1,4-dideoxy-1,4-imino-L-threitol and 1,4-dideoxy-1,4-imino-L-arabinitol. |
| title_sort | inhibition of the alpha l arabinofuranosidase iii of monilinia fructigena by 1 4 dideoxy 1 4 imino l threitol and 1 4 dideoxy 1 4 imino l arabinitol |
| work_keys_str_mv | AT axamawatym inhibitionofthealphalarabinofuranosidaseiiiofmoniliniafructigenaby14dideoxy14iminolthreitoland14dideoxy14iminolarabinitol AT fleetg inhibitionofthealphalarabinofuranosidaseiiiofmoniliniafructigenaby14dideoxy14iminolthreitoland14dideoxy14iminolarabinitol AT hannahk inhibitionofthealphalarabinofuranosidaseiiiofmoniliniafructigenaby14dideoxy14iminolthreitoland14dideoxy14iminolarabinitol AT namgoongs inhibitionofthealphalarabinofuranosidaseiiiofmoniliniafructigenaby14dideoxy14iminolthreitoland14dideoxy14iminolarabinitol AT sinnottm inhibitionofthealphalarabinofuranosidaseiiiofmoniliniafructigenaby14dideoxy14iminolthreitoland14dideoxy14iminolarabinitol |