دورية أكاديمية
Solid-phase total synthesis of trunkamide A(1).
| العنوان: | Solid-phase total synthesis of trunkamide A(1). |
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| المؤلفون: | Caba JM; The Department of Organic Chemistry, University of Barcelona, 08028 Barcelona, Spain., Rodriguez IM, Manzanares I, Giralt E, Albericio F |
| المصدر: | The Journal of organic chemistry [J Org Chem] 2001 Nov 16; Vol. 66 (23), pp. 7568-74. |
| نوع المنشور: | Journal Article; Research Support, Non-U.S. Gov't |
| اللغة: | English |
| بيانات الدورية: | Publisher: American Chemical Society Country of Publication: United States NLM ID: 2985193R Publication Model: Print Cited Medium: Print ISSN: 0022-3263 (Print) Linking ISSN: 00223263 NLM ISO Abbreviation: J Org Chem Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: Columbus Oh : American Chemical Society Original Publication: Easton, Pa. [etc.] |
| مواضيع طبية MeSH: | Peptides, Cyclic/*chemical synthesis, Animals ; Antineoplastic Agents/chemical synthesis ; Urochordata/chemistry |
| مستخلص: | Marine organisms are a rich source of novel, biologically active compounds. Herein, the solid-phase total synthesis of trunkamide A, currently in preclinical trials, is presented. Trunkamide A contains a thiazoline heterocycle and two residues of Ser and Thr with the hydroxy function modified as reverse prenyl (rPr). Cornerstones of the synthesis are as follows: (i) solid-phase peptide chain elongation using a quasi-orthogonal protecting scheme with tert-butyl and fluorenyl based groups, on a chlorotrityl resin; (ii) concourse of HOAt-based coupling reagents; and (iii) cyclizations in solution. Furthermore, the following synthetic steps are discussed: (i) preparation of the reverse prenyl derivatives of Ser and Thr; (ii) introduction of precursor of thiazoline as a protected amino thionoacid derivative; and (iii) formation of the thiazoline ring with DAST. All these features make this strategy particularly suitable for the large-scale synthesis of trunkamide A and other peptides containing the same motifs. |
| المشرفين على المادة: | 0 (Antineoplastic Agents) 0 (Peptides, Cyclic) 0 (trunkamide A) |
| تواريخ الأحداث: | Date Created: 20011110 Date Completed: 20020122 Latest Revision: 20190710 |
| رمز التحديث: | 20231215 |
| DOI: | 10.1021/jo015703t |
| PMID: | 11701007 |
| قاعدة البيانات: | MEDLINE |
Find this issue from the American Chemical Society | تدمد: | 0022-3263 |
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| DOI: | 10.1021/jo015703t |