Eintrag weiter verarbeiten
Catalytic activation of glycosyl phosphates for stereoselective coupling reactions
Gespeichert in:
| Zeitschriftentitel: | Proceedings of the National Academy of Sciences |
|---|---|
| Personen und Körperschaften: | , , , |
| In: | Proceedings of the National Academy of Sciences, 116, 2019, 1, S. 35-39 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Proceedings of the National Academy of Sciences
|
| Schlagwörter: |
| author_facet |
Levi, Samuel M. Li, Qiuhan Rötheli, Andreas R. Jacobsen, Eric N. Levi, Samuel M. Li, Qiuhan Rötheli, Andreas R. Jacobsen, Eric N. |
|---|---|
| author |
Levi, Samuel M. Li, Qiuhan Rötheli, Andreas R. Jacobsen, Eric N. |
| spellingShingle |
Levi, Samuel M. Li, Qiuhan Rötheli, Andreas R. Jacobsen, Eric N. Proceedings of the National Academy of Sciences Catalytic activation of glycosyl phosphates for stereoselective coupling reactions Multidisciplinary |
| author_sort |
levi, samuel m. |
| spelling |
Levi, Samuel M. Li, Qiuhan Rötheli, Andreas R. Jacobsen, Eric N. 0027-8424 1091-6490 Proceedings of the National Academy of Sciences Multidisciplinary http://dx.doi.org/10.1073/pnas.1811186116 <jats:title>Significance</jats:title> <jats:p>Despite their dominant role as electrophiles in biosynthetic pathways promoted by enzymes, organic phosphates are rarely employed in laboratory synthesis, because phosphates are generally very poor leaving groups. Here we report that a bis-thiourea catalyst promotes β-selective glycosylation reactions of phosphate donors under mild, neutral conditions. The catalytic method enables glycosylation of peptides, complex natural products, and pharmaceutical agents bearing a variety of reactive functionalities, thereby representing an important step toward enabling convenient access to glycosylated chemical matter of interest to synthetic chemists and chemical biologists.</jats:p> Catalytic activation of glycosyl phosphates for stereoselective coupling reactions Proceedings of the National Academy of Sciences |
| doi_str_mv |
10.1073/pnas.1811186116 |
| facet_avail |
Online Free |
| format |
ElectronicArticle |
| fullrecord |
blob:ai-49-aHR0cDovL2R4LmRvaS5vcmcvMTAuMTA3My9wbmFzLjE4MTExODYxMTY |
| id |
ai-49-aHR0cDovL2R4LmRvaS5vcmcvMTAuMTA3My9wbmFzLjE4MTExODYxMTY |
| institution |
DE-D275 DE-Bn3 DE-Brt1 DE-Zwi2 DE-D161 DE-Gla1 DE-Zi4 DE-15 DE-Pl11 DE-Rs1 DE-105 DE-14 DE-Ch1 DE-L229 |
| imprint |
Proceedings of the National Academy of Sciences, 2019 |
| imprint_str_mv |
Proceedings of the National Academy of Sciences, 2019 |
| issn |
0027-8424 1091-6490 |
| issn_str_mv |
0027-8424 1091-6490 |
| language |
English |
| mega_collection |
Proceedings of the National Academy of Sciences (CrossRef) |
| match_str |
levi2019catalyticactivationofglycosylphosphatesforstereoselectivecouplingreactions |
| publishDateSort |
2019 |
| publisher |
Proceedings of the National Academy of Sciences |
| recordtype |
ai |
| record_format |
ai |
| series |
Proceedings of the National Academy of Sciences |
| source_id |
49 |
| title |
Catalytic activation of glycosyl phosphates for stereoselective coupling reactions |
| title_unstemmed |
Catalytic activation of glycosyl phosphates for stereoselective coupling reactions |
| title_full |
Catalytic activation of glycosyl phosphates for stereoselective coupling reactions |
| title_fullStr |
Catalytic activation of glycosyl phosphates for stereoselective coupling reactions |
| title_full_unstemmed |
Catalytic activation of glycosyl phosphates for stereoselective coupling reactions |
| title_short |
Catalytic activation of glycosyl phosphates for stereoselective coupling reactions |
| title_sort |
catalytic activation of glycosyl phosphates for stereoselective coupling reactions |
| topic |
Multidisciplinary |
| url |
http://dx.doi.org/10.1073/pnas.1811186116 |
| publishDate |
2019 |
| physical |
35-39 |
| description |
<jats:title>Significance</jats:title>
<jats:p>Despite their dominant role as electrophiles in biosynthetic pathways promoted by enzymes, organic phosphates are rarely employed in laboratory synthesis, because phosphates are generally very poor leaving groups. Here we report that a bis-thiourea catalyst promotes β-selective glycosylation reactions of phosphate donors under mild, neutral conditions. The catalytic method enables glycosylation of peptides, complex natural products, and pharmaceutical agents bearing a variety of reactive functionalities, thereby representing an important step toward enabling convenient access to glycosylated chemical matter of interest to synthetic chemists and chemical biologists.</jats:p> |
| container_issue |
1 |
| container_start_page |
35 |
| container_title |
Proceedings of the National Academy of Sciences |
| container_volume |
116 |
| format_de105 |
Article, E-Article |
| format_de14 |
Article, E-Article |
| format_de15 |
Article, E-Article |
| format_de520 |
Article, E-Article |
| format_de540 |
Article, E-Article |
| format_dech1 |
Article, E-Article |
| format_ded117 |
Article, E-Article |
| format_degla1 |
E-Article |
| format_del152 |
Buch |
| format_del189 |
Article, E-Article |
| format_dezi4 |
Article |
| format_dezwi2 |
Article, E-Article |
| format_finc |
Article, E-Article |
| format_nrw |
Article, E-Article |
| _version_ |
1792347583008473088 |
| geogr_code |
not assigned |
| last_indexed |
2024-03-01T17:57:35.33Z |
| geogr_code_person |
not assigned |
| openURL |
url_ver=Z39.88-2004&ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fvufind.svn.sourceforge.net%3Agenerator&rft.title=Catalytic+activation+of+glycosyl+phosphates+for+stereoselective+coupling+reactions&rft.date=2019-01-02&genre=article&issn=1091-6490&volume=116&issue=1&spage=35&epage=39&pages=35-39&jtitle=Proceedings+of+the+National+Academy+of+Sciences&atitle=Catalytic+activation+of+glycosyl+phosphates+for+stereoselective+coupling+reactions&aulast=Jacobsen&aufirst=Eric+N.&rft_id=info%3Adoi%2F10.1073%2Fpnas.1811186116&rft.language%5B0%5D=eng |
| SOLR | |
| _version_ | 1792347583008473088 |
| author | Levi, Samuel M., Li, Qiuhan, Rötheli, Andreas R., Jacobsen, Eric N. |
| author_facet | Levi, Samuel M., Li, Qiuhan, Rötheli, Andreas R., Jacobsen, Eric N., Levi, Samuel M., Li, Qiuhan, Rötheli, Andreas R., Jacobsen, Eric N. |
| author_sort | levi, samuel m. |
| container_issue | 1 |
| container_start_page | 35 |
| container_title | Proceedings of the National Academy of Sciences |
| container_volume | 116 |
| description | <jats:title>Significance</jats:title> <jats:p>Despite their dominant role as electrophiles in biosynthetic pathways promoted by enzymes, organic phosphates are rarely employed in laboratory synthesis, because phosphates are generally very poor leaving groups. Here we report that a bis-thiourea catalyst promotes β-selective glycosylation reactions of phosphate donors under mild, neutral conditions. The catalytic method enables glycosylation of peptides, complex natural products, and pharmaceutical agents bearing a variety of reactive functionalities, thereby representing an important step toward enabling convenient access to glycosylated chemical matter of interest to synthetic chemists and chemical biologists.</jats:p> |
| doi_str_mv | 10.1073/pnas.1811186116 |
| facet_avail | Online, Free |
| format | ElectronicArticle |
| format_de105 | Article, E-Article |
| format_de14 | Article, E-Article |
| format_de15 | Article, E-Article |
| format_de520 | Article, E-Article |
| format_de540 | Article, E-Article |
| format_dech1 | Article, E-Article |
| format_ded117 | Article, E-Article |
| format_degla1 | E-Article |
| format_del152 | Buch |
| format_del189 | Article, E-Article |
| format_dezi4 | Article |
| format_dezwi2 | Article, E-Article |
| format_finc | Article, E-Article |
| format_nrw | Article, E-Article |
| geogr_code | not assigned |
| geogr_code_person | not assigned |
| id | ai-49-aHR0cDovL2R4LmRvaS5vcmcvMTAuMTA3My9wbmFzLjE4MTExODYxMTY |
| imprint | Proceedings of the National Academy of Sciences, 2019 |
| imprint_str_mv | Proceedings of the National Academy of Sciences, 2019 |
| institution | DE-D275, DE-Bn3, DE-Brt1, DE-Zwi2, DE-D161, DE-Gla1, DE-Zi4, DE-15, DE-Pl11, DE-Rs1, DE-105, DE-14, DE-Ch1, DE-L229 |
| issn | 0027-8424, 1091-6490 |
| issn_str_mv | 0027-8424, 1091-6490 |
| language | English |
| last_indexed | 2024-03-01T17:57:35.33Z |
| match_str | levi2019catalyticactivationofglycosylphosphatesforstereoselectivecouplingreactions |
| mega_collection | Proceedings of the National Academy of Sciences (CrossRef) |
| physical | 35-39 |
| publishDate | 2019 |
| publishDateSort | 2019 |
| publisher | Proceedings of the National Academy of Sciences |
| record_format | ai |
| recordtype | ai |
| series | Proceedings of the National Academy of Sciences |
| source_id | 49 |
| spelling | Levi, Samuel M. Li, Qiuhan Rötheli, Andreas R. Jacobsen, Eric N. 0027-8424 1091-6490 Proceedings of the National Academy of Sciences Multidisciplinary http://dx.doi.org/10.1073/pnas.1811186116 <jats:title>Significance</jats:title> <jats:p>Despite their dominant role as electrophiles in biosynthetic pathways promoted by enzymes, organic phosphates are rarely employed in laboratory synthesis, because phosphates are generally very poor leaving groups. Here we report that a bis-thiourea catalyst promotes β-selective glycosylation reactions of phosphate donors under mild, neutral conditions. The catalytic method enables glycosylation of peptides, complex natural products, and pharmaceutical agents bearing a variety of reactive functionalities, thereby representing an important step toward enabling convenient access to glycosylated chemical matter of interest to synthetic chemists and chemical biologists.</jats:p> Catalytic activation of glycosyl phosphates for stereoselective coupling reactions Proceedings of the National Academy of Sciences |
| spellingShingle | Levi, Samuel M., Li, Qiuhan, Rötheli, Andreas R., Jacobsen, Eric N., Proceedings of the National Academy of Sciences, Catalytic activation of glycosyl phosphates for stereoselective coupling reactions, Multidisciplinary |
| title | Catalytic activation of glycosyl phosphates for stereoselective coupling reactions |
| title_full | Catalytic activation of glycosyl phosphates for stereoselective coupling reactions |
| title_fullStr | Catalytic activation of glycosyl phosphates for stereoselective coupling reactions |
| title_full_unstemmed | Catalytic activation of glycosyl phosphates for stereoselective coupling reactions |
| title_short | Catalytic activation of glycosyl phosphates for stereoselective coupling reactions |
| title_sort | catalytic activation of glycosyl phosphates for stereoselective coupling reactions |
| title_unstemmed | Catalytic activation of glycosyl phosphates for stereoselective coupling reactions |
| topic | Multidisciplinary |
| url | http://dx.doi.org/10.1073/pnas.1811186116 |