First chemoenzymatic synthesis of immunomodulating macrolactam pimecrolimus
The preparation of pimecrolimus, a synthetic derivative of ascomycin endowed with immunomodulatory activity, requires the selective protection of 24-hydroxy group of the ascomycin, before elaboration of the 32 one. The aim was achieved by means of two regioselective Candida antarctica lipase-catalyz...
| Published in: | Tetrahedron Letters |
|---|---|
| Main Authors: | , , , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
Elsevier
2009
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| Subjects: | |
| Online Access: | http://hdl.handle.net/2434/66629 https://doi.org/10.1016/j.tetlet.2009.05.066 |
| _version_ | 1821748173756956672 |
|---|---|
| author | P. Ferraboschi D. Colombo M. De Mieri P. Grisenti |
| author2 | P. Ferraboschi D. Colombo M. De Mieri P. Grisenti |
| author_facet | P. Ferraboschi D. Colombo M. De Mieri P. Grisenti |
| author_sort | P. Ferraboschi |
| collection | The University of Milan: Archivio Istituzionale della Ricerca (AIR) |
| container_issue | 30 |
| container_start_page | 4384 |
| container_title | Tetrahedron Letters |
| container_volume | 50 |
| description | The preparation of pimecrolimus, a synthetic derivative of ascomycin endowed with immunomodulatory activity, requires the selective protection of 24-hydroxy group of the ascomycin, before elaboration of the 32 one. The aim was achieved by means of two regioselective Candida antarctica lipase-catalyzed steps. The structure of the new key intermediates, 24-, 32-monoacetates and 24,32-diacetate, was established by means of an unambiguous NMR study. |
| format | Article in Journal/Newspaper |
| genre | Antarc* Antarctica |
| genre_facet | Antarc* Antarctica |
| id | ftunivmilanoair:oai:air.unimi.it:2434/66629 |
| institution | Open Polar |
| language | English |
| op_collection_id | ftunivmilanoair |
| op_container_end_page | 4388 |
| op_doi | https://doi.org/10.1016/j.tetlet.2009.05.066 |
| op_relation | info:eu-repo/semantics/altIdentifier/wos/WOS:000267495900023 volume:50 issue:30 firstpage:4384 lastpage:4388 journal:TETRAHEDRON LETTERS http://hdl.handle.net/2434/66629 doi:10.1016/j.tetlet.2009.05.066 info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-66749138208 |
| publishDate | 2009 |
| publisher | Elsevier |
| record_format | openpolar |
| spelling | ftunivmilanoair:oai:air.unimi.it:2434/66629 2025-01-16T19:19:44+00:00 First chemoenzymatic synthesis of immunomodulating macrolactam pimecrolimus P. Ferraboschi D. Colombo M. De Mieri P. Grisenti P. Ferraboschi D. Colombo M. De Mieri P. Grisenti 2009-07-29 http://hdl.handle.net/2434/66629 https://doi.org/10.1016/j.tetlet.2009.05.066 eng eng Elsevier info:eu-repo/semantics/altIdentifier/wos/WOS:000267495900023 volume:50 issue:30 firstpage:4384 lastpage:4388 journal:TETRAHEDRON LETTERS http://hdl.handle.net/2434/66629 doi:10.1016/j.tetlet.2009.05.066 info:eu-repo/semantics/altIdentifier/scopus/2-s2.0-66749138208 Ascomycin Immunomodulator Lipase Macrolactam Regioselectivity Settore BIO/10 - Biochimica info:eu-repo/semantics/article 2009 ftunivmilanoair https://doi.org/10.1016/j.tetlet.2009.05.066 2024-01-09T23:22:18Z The preparation of pimecrolimus, a synthetic derivative of ascomycin endowed with immunomodulatory activity, requires the selective protection of 24-hydroxy group of the ascomycin, before elaboration of the 32 one. The aim was achieved by means of two regioselective Candida antarctica lipase-catalyzed steps. The structure of the new key intermediates, 24-, 32-monoacetates and 24,32-diacetate, was established by means of an unambiguous NMR study. Article in Journal/Newspaper Antarc* Antarctica The University of Milan: Archivio Istituzionale della Ricerca (AIR) Tetrahedron Letters 50 30 4384 4388 |
| spellingShingle | Ascomycin Immunomodulator Lipase Macrolactam Regioselectivity Settore BIO/10 - Biochimica P. Ferraboschi D. Colombo M. De Mieri P. Grisenti First chemoenzymatic synthesis of immunomodulating macrolactam pimecrolimus |
| title | First chemoenzymatic synthesis of immunomodulating macrolactam pimecrolimus |
| title_full | First chemoenzymatic synthesis of immunomodulating macrolactam pimecrolimus |
| title_fullStr | First chemoenzymatic synthesis of immunomodulating macrolactam pimecrolimus |
| title_full_unstemmed | First chemoenzymatic synthesis of immunomodulating macrolactam pimecrolimus |
| title_short | First chemoenzymatic synthesis of immunomodulating macrolactam pimecrolimus |
| title_sort | first chemoenzymatic synthesis of immunomodulating macrolactam pimecrolimus |
| topic | Ascomycin Immunomodulator Lipase Macrolactam Regioselectivity Settore BIO/10 - Biochimica |
| topic_facet | Ascomycin Immunomodulator Lipase Macrolactam Regioselectivity Settore BIO/10 - Biochimica |
| url | http://hdl.handle.net/2434/66629 https://doi.org/10.1016/j.tetlet.2009.05.066 |