Pteridines CVII* Synthesis of 6-Azidomethyl-5,6,7,8-tetrahydropterin. Photo degradation Products and Cofactor Properties on Aromatic Amino Acid Monooxygenases
The synthesis of 6-azidomethyl-5,6,7,8-tetrahydropterin (6-AzmH4Ptr) (9) starting from 2,4-diamino- 6-hydroxymethylpteridine (1) is described. A special protecting group strategy had to be applied to perform the structural modifications. The introduction of the azido function was achieved by a Mitsu...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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De Gruyter
1995-11-01
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| Series: | Pteridines |
| Subjects: | |
| Online Access: | https://doi.org/10.1515/pteridines.1995.6.4.153 |
| _version_ | 1818737977203884032 |
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| author | Heizmann Gerhard Groehn Viola Almås Bjørg Haavik Jan Flatmark Torgeir Pfleiderer Wolfgang |
| author_facet | Heizmann Gerhard Groehn Viola Almås Bjørg Haavik Jan Flatmark Torgeir Pfleiderer Wolfgang |
| author_sort | Heizmann Gerhard |
| collection | DOAJ |
| description | The synthesis of 6-azidomethyl-5,6,7,8-tetrahydropterin (6-AzmH4Ptr) (9) starting from 2,4-diamino- 6-hydroxymethylpteridine (1) is described. A special protecting group strategy had to be applied to perform the structural modifications. The introduction of the azido function was achieved by a Mitsunobu reaction converting the N2 - N ,N -dimethylaminomethylen-6 -hydroxymethyl-5-pivaloyl-5,6,7 ,8-tetrahydropterin (7) with diphenylphosphoryl azide into the corresponding 6-azidomethyl derivative (8). The newly synthesized compounds have been characterized by elemental analyses, UV, IR and 1H-NMR spectra. The photolysis of 6-AzmH4Ptr (9) and its inactivation effect upon aromatic amino acid mono oxygenases has been studied |
| first_indexed | 2024-12-18T01:01:37Z |
| format | Article |
| id | doaj.art-04a5e31a724b4d1f9feb84c57ea8cff8 |
| institution | Directory Open Access Journal |
| issn | 0933-4807 2195-4720 |
| language | English |
| last_indexed | 2024-12-18T01:01:37Z |
| publishDate | 1995-11-01 |
| publisher | De Gruyter |
| record_format | Article |
| series | Pteridines |
| spelling | doaj.art-04a5e31a724b4d1f9feb84c57ea8cff82022-12-21T21:26:21ZengDe GruyterPteridines0933-48072195-47201995-11-016415315910.1515/pteridines.1995.6.4.153Pteridines CVII* Synthesis of 6-Azidomethyl-5,6,7,8-tetrahydropterin. Photo degradation Products and Cofactor Properties on Aromatic Amino Acid MonooxygenasesHeizmann Gerhard0Groehn Viola1Almås Bjørg2Haavik Jan3Flatmark Torgeir4Pfleiderer Wolfgang5Fakultat für Chemie, Universität Konstanz, Postfach 5560, D -78434 Konstanz/GermanyFakultat für Chemie, Universität Konstanz, Postfach 5560, D -78434 Konstanz/GermanyDept. of Biochemistry and Molecular Biology, University of Bergen, Arstadveien 19, N-5009 Bergen/Norway.Dept. of Biochemistry and Molecular Biology, University of Bergen, Arstadveien 19, N-5009 Bergen/Norway.Dept. of Biochemistry and Molecular Biology, University of Bergen, Arstadveien 19, N-5009 Bergen/Norway.Fakultat für Chemie, Universität Konstanz, Postfach 5560, D -78434 Konstanz/GermanyThe synthesis of 6-azidomethyl-5,6,7,8-tetrahydropterin (6-AzmH4Ptr) (9) starting from 2,4-diamino- 6-hydroxymethylpteridine (1) is described. A special protecting group strategy had to be applied to perform the structural modifications. The introduction of the azido function was achieved by a Mitsunobu reaction converting the N2 - N ,N -dimethylaminomethylen-6 -hydroxymethyl-5-pivaloyl-5,6,7 ,8-tetrahydropterin (7) with diphenylphosphoryl azide into the corresponding 6-azidomethyl derivative (8). The newly synthesized compounds have been characterized by elemental analyses, UV, IR and 1H-NMR spectra. The photolysis of 6-AzmH4Ptr (9) and its inactivation effect upon aromatic amino acid mono oxygenases has been studiedhttps://doi.org/10.1515/pteridines.1995.6.4.153tetrahydropterinscofactorphotodegradationmonooxygenasesmitsunobu reactionazidomethyl group |
| spellingShingle | Heizmann Gerhard Groehn Viola Almås Bjørg Haavik Jan Flatmark Torgeir Pfleiderer Wolfgang Pteridines CVII* Synthesis of 6-Azidomethyl-5,6,7,8-tetrahydropterin. Photo degradation Products and Cofactor Properties on Aromatic Amino Acid Monooxygenases Pteridines tetrahydropterins cofactor photodegradation monooxygenases mitsunobu reaction azidomethyl group |
| title | Pteridines CVII* Synthesis of 6-Azidomethyl-5,6,7,8-tetrahydropterin. Photo degradation Products and Cofactor Properties on Aromatic Amino Acid Monooxygenases |
| title_full | Pteridines CVII* Synthesis of 6-Azidomethyl-5,6,7,8-tetrahydropterin. Photo degradation Products and Cofactor Properties on Aromatic Amino Acid Monooxygenases |
| title_fullStr | Pteridines CVII* Synthesis of 6-Azidomethyl-5,6,7,8-tetrahydropterin. Photo degradation Products and Cofactor Properties on Aromatic Amino Acid Monooxygenases |
| title_full_unstemmed | Pteridines CVII* Synthesis of 6-Azidomethyl-5,6,7,8-tetrahydropterin. Photo degradation Products and Cofactor Properties on Aromatic Amino Acid Monooxygenases |
| title_short | Pteridines CVII* Synthesis of 6-Azidomethyl-5,6,7,8-tetrahydropterin. Photo degradation Products and Cofactor Properties on Aromatic Amino Acid Monooxygenases |
| title_sort | pteridines cvii synthesis of 6 azidomethyl 5 6 7 8 tetrahydropterin photo degradation products and cofactor properties on aromatic amino acid monooxygenases |
| topic | tetrahydropterins cofactor photodegradation monooxygenases mitsunobu reaction azidomethyl group |
| url | https://doi.org/10.1515/pteridines.1995.6.4.153 |
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