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Synthesis of a Versatile Building Block for the Preparation of 6-N-Derivatized α-Galactosyl Ceramides: Rapid Access to Biologically Active Glycolipids
[Image: see text] A concise route to the 6-azido-6-deoxy-α-galactosyl-phytosphingosine derivative 9 is reported. Orthogonal protection of the two amino groups allows elaboration of 9 into a range of 6-N-derivatized α-galactosyl ceramides by late-stage introduction of the acyl chain of the ceramide a...
| Autores principales: | , , |
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| Formato: | Texto |
| Lenguaje: | English |
| Publicado: |
American Chemical Society
2010
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| Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3018865/ https://www.ncbi.nlm.nih.gov/pubmed/21155575 http://dx.doi.org/10.1021/jo102064p |
| _version_ | 1782196124201779200 |
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| author | Jervis, Peter J. Cox, Liam R. Besra, Gurdyal S. |
| author_facet | Jervis, Peter J. Cox, Liam R. Besra, Gurdyal S. |
| author_sort | Jervis, Peter J. |
| collection | PubMed |
| description | [Image: see text] A concise route to the 6-azido-6-deoxy-α-galactosyl-phytosphingosine derivative 9 is reported. Orthogonal protection of the two amino groups allows elaboration of 9 into a range of 6-N-derivatized α-galactosyl ceramides by late-stage introduction of the acyl chain of the ceramide and the 6-N-group in the sugar headgroup. Biologically active glycolipids 6 and 8 have been synthesized to illustrate the applicability of the approach. |
| format | Text |
| id | pubmed-3018865 |
| institution | National Center for Biotechnology Information |
| language | English |
| publishDate | 2010 |
| publisher | American Chemical Society |
| record_format | MEDLINE/PubMed |
| spelling | pubmed-30188652011-01-11 Synthesis of a Versatile Building Block for the Preparation of 6-N-Derivatized α-Galactosyl Ceramides: Rapid Access to Biologically Active Glycolipids Jervis, Peter J. Cox, Liam R. Besra, Gurdyal S. J Org Chem [Image: see text] A concise route to the 6-azido-6-deoxy-α-galactosyl-phytosphingosine derivative 9 is reported. Orthogonal protection of the two amino groups allows elaboration of 9 into a range of 6-N-derivatized α-galactosyl ceramides by late-stage introduction of the acyl chain of the ceramide and the 6-N-group in the sugar headgroup. Biologically active glycolipids 6 and 8 have been synthesized to illustrate the applicability of the approach. American Chemical Society 2010-12-14 2011-01-07 /pmc/articles/PMC3018865/ /pubmed/21155575 http://dx.doi.org/10.1021/jo102064p Text en Copyright © 2010 American Chemical Society http://pubs.acs.org This is an open-access article distributed under the ACS AuthorChoice Terms & Conditions. Any use of this article, must conform to the terms of that license which are available at http://pubs.acs.org. |
| spellingShingle | Jervis, Peter J. Cox, Liam R. Besra, Gurdyal S. Synthesis of a Versatile Building Block for the Preparation of 6-N-Derivatized α-Galactosyl Ceramides: Rapid Access to Biologically Active Glycolipids |
| title | Synthesis of a Versatile Building Block for the Preparation of 6-N-Derivatized α-Galactosyl Ceramides: Rapid Access to Biologically Active Glycolipids |
| title_full | Synthesis of a Versatile Building Block for the Preparation of 6-N-Derivatized α-Galactosyl Ceramides: Rapid Access to Biologically Active Glycolipids |
| title_fullStr | Synthesis of a Versatile Building Block for the Preparation of 6-N-Derivatized α-Galactosyl Ceramides: Rapid Access to Biologically Active Glycolipids |
| title_full_unstemmed | Synthesis of a Versatile Building Block for the Preparation of 6-N-Derivatized α-Galactosyl Ceramides: Rapid Access to Biologically Active Glycolipids |
| title_short | Synthesis of a Versatile Building Block for the Preparation of 6-N-Derivatized α-Galactosyl Ceramides: Rapid Access to Biologically Active Glycolipids |
| title_sort | synthesis of a versatile building block for the preparation of 6-n-derivatized α-galactosyl ceramides: rapid access to biologically active glycolipids |
| url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3018865/ https://www.ncbi.nlm.nih.gov/pubmed/21155575 http://dx.doi.org/10.1021/jo102064p |
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