Preparation of new alkyne-modified ansamitocins by mutasynthesis
The preparation of alkyne-modified ansamitocins by mutasynthetic supplementation of Actinosynnema pretiosum mutants with alkyne-substituted aminobenzoic acids is described. This modification paved the way to introduce a thiol linker by Huisgen-type cycloaddition which can principally be utilized to...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2014-03-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.49 |
| _version_ | 1818416463669624832 |
|---|---|
| author | Kirsten Harmrolfs Lena Mancuso Binia Drung Florenz Sasse Andreas Kirschning |
| author_facet | Kirsten Harmrolfs Lena Mancuso Binia Drung Florenz Sasse Andreas Kirschning |
| author_sort | Kirsten Harmrolfs |
| collection | DOAJ |
| description | The preparation of alkyne-modified ansamitocins by mutasynthetic supplementation of Actinosynnema pretiosum mutants with alkyne-substituted aminobenzoic acids is described. This modification paved the way to introduce a thiol linker by Huisgen-type cycloaddition which can principally be utilized to create tumor targeting conjugates. In bioactivity tests, only those new ansamitocin derivatives showed strong antiproliferative activity that bear an ester side chain at C-3. |
| first_indexed | 2024-12-14T11:51:17Z |
| format | Article |
| id | doaj.art-8d6498ead2da499897a399bf28f3115a |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-14T11:51:17Z |
| publishDate | 2014-03-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-8d6498ead2da499897a399bf28f3115a2022-12-21T23:02:17ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-03-0110153554310.3762/bjoc.10.491860-5397-10-49Preparation of new alkyne-modified ansamitocins by mutasynthesisKirsten Harmrolfs0Lena Mancuso1Binia Drung2Florenz Sasse3Andreas Kirschning4Institute of Organic Chemistry and Center of Biomolecular Drug Research (BMWZ), Leibniz University Hannover, Schneiderberg 1b, 30167 Hannover, GermanyInstitute of Organic Chemistry and Center of Biomolecular Drug Research (BMWZ), Leibniz University Hannover, Schneiderberg 1b, 30167 Hannover, GermanyInstitute of Organic Chemistry and Center of Biomolecular Drug Research (BMWZ), Leibniz University Hannover, Schneiderberg 1b, 30167 Hannover, GermanyDepartment of Chemical Biology, Helmholtz Center for Infectious Research (HZI), Inhoffenstraße 7, D-38124 Braunschweig, GermanyInstitute of Organic Chemistry and Center of Biomolecular Drug Research (BMWZ), Leibniz University Hannover, Schneiderberg 1b, 30167 Hannover, GermanyThe preparation of alkyne-modified ansamitocins by mutasynthetic supplementation of Actinosynnema pretiosum mutants with alkyne-substituted aminobenzoic acids is described. This modification paved the way to introduce a thiol linker by Huisgen-type cycloaddition which can principally be utilized to create tumor targeting conjugates. In bioactivity tests, only those new ansamitocin derivatives showed strong antiproliferative activity that bear an ester side chain at C-3.https://doi.org/10.3762/bjoc.10.49ansamitocinsantibioticsantitumor agentsclick chemistrymutasynthesisnatural products |
| spellingShingle | Kirsten Harmrolfs Lena Mancuso Binia Drung Florenz Sasse Andreas Kirschning Preparation of new alkyne-modified ansamitocins by mutasynthesis Beilstein Journal of Organic Chemistry ansamitocins antibiotics antitumor agents click chemistry mutasynthesis natural products |
| title | Preparation of new alkyne-modified ansamitocins by mutasynthesis |
| title_full | Preparation of new alkyne-modified ansamitocins by mutasynthesis |
| title_fullStr | Preparation of new alkyne-modified ansamitocins by mutasynthesis |
| title_full_unstemmed | Preparation of new alkyne-modified ansamitocins by mutasynthesis |
| title_short | Preparation of new alkyne-modified ansamitocins by mutasynthesis |
| title_sort | preparation of new alkyne modified ansamitocins by mutasynthesis |
| topic | ansamitocins antibiotics antitumor agents click chemistry mutasynthesis natural products |
| url | https://doi.org/10.3762/bjoc.10.49 |
| work_keys_str_mv | AT kirstenharmrolfs preparationofnewalkynemodifiedansamitocinsbymutasynthesis AT lenamancuso preparationofnewalkynemodifiedansamitocinsbymutasynthesis AT biniadrung preparationofnewalkynemodifiedansamitocinsbymutasynthesis AT florenzsasse preparationofnewalkynemodifiedansamitocinsbymutasynthesis AT andreaskirschning preparationofnewalkynemodifiedansamitocinsbymutasynthesis |