دورية أكاديمية
Investigation into an efficient synthesis of 2,3-dehydro-N-acetyl neuraminic acid leads to three decarboxylated sialic acid dimers.
| العنوان: | Investigation into an efficient synthesis of 2,3-dehydro-N-acetyl neuraminic acid leads to three decarboxylated sialic acid dimers. |
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| المؤلفون: | Horn EJ; Department of Chemistry, University of California-Davis, One Shields Avenue, Davis, CA 95616, USA., Saludes JP, Gervay-Hague J |
| المصدر: | Carbohydrate research [Carbohydr Res] 2008 Apr 07; Vol. 343 (5), pp. 936-40. Date of Electronic Publication: 2008 Feb 02. |
| نوع المنشور: | Journal Article; Research Support, N.I.H., Extramural; Research Support, U.S. Gov't, Non-P.H.S. |
| اللغة: | English |
| بيانات الدورية: | Publisher: Elsevier Country of Publication: Netherlands NLM ID: 0043535 Publication Model: Print-Electronic Cited Medium: Print ISSN: 0008-6215 (Print) Linking ISSN: 00086215 NLM ISO Abbreviation: Carbohydr Res Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: Amsterdam : Elsevier Original Publication: Amsterdam. |
| مواضيع طبية MeSH: | N-Acetylneuraminic Acid/*chemical synthesis , Neuraminic Acids/*chemical synthesis , Sialic Acids/*chemical synthesis, Decarboxylation ; Dimerization ; Magnetic Resonance Spectroscopy ; Mass Spectrometry ; Models, Chemical ; Molecular Structure ; N-Acetylneuraminic Acid/analogs & derivatives ; N-Acetylneuraminic Acid/chemistry ; Neuraminic Acids/chemistry ; Sialic Acids/chemistry |
| مستخلص: | Sialic acid, an important carbohydrate found incorporated on the cell surface of many organisms, has been modified for use in a wide range of biological and pharmaceutical applications. We hypothesized that 4,7,8,9-tetra-O-acetyl-2-deoxy-2,3-dehydro-N-acetyl neuraminic acid methyl ester (4) could be efficiently synthesized in a one-pot reaction by heating peracetylated sialic acid (2) in pyridine and acetic anhydride to induce beta-elimination. When reduced to practice, this reaction produced only modest yields of 4. Six compounds, including three new decarboxylated sialic acid dimers, were also found to have been synthesized in the reaction. In an effort to better understand the chemistry and the mechanisms of this reaction, all of the side products were isolated and fully characterized. |
| معلومات مُعتمدة: | RR 1973 United States RR NCRR NIH HHS |
| المشرفين على المادة: | 0 (4,7,8,9-tetra-O-acetyl-N-acetyl-2,3-dehydro-2-deoxy-4-neuraminic acid methyl ester) 0 (Neuraminic Acids) 0 (Sialic Acids) 24967-27-9 (2-deoxy-2,3-dehydro-N-acetylneuraminic acid) GZP2782OP0 (N-Acetylneuraminic Acid) |
| تواريخ الأحداث: | Date Created: 20080220 Date Completed: 20080602 Latest Revision: 20131121 |
| رمز التحديث: | 20240628 |
| DOI: | 10.1016/j.carres.2008.01.033 |
| PMID: | 18282561 |
| قاعدة البيانات: | MEDLINE |
Full Text Finder | تدمد: | 0008-6215 |
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| DOI: | 10.1016/j.carres.2008.01.033 |