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杀稻瘟菌素全合成的一种方法。

An approach to the total synthesis of sinefungin.

作者信息

Mock G A, Moffatt J G

出版信息

Nucleic Acids Res. 1982 Oct 25;10(20):6223-34. doi: 10.1093/nar/10.20.6223.

DOI:10.1093/nar/10.20.6223
PMID:7177844
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC326912/
Abstract

Condensation of N6-benzoyl-2',3'-O-isopropylideneadenosine-5'-aldehyde with nitromethane followed by acid catalyzed acetylation and borohydride reduction leads to N6-benzoyl-9-(5,6-dideoxy-2,3-O-isopropylidene-6-nitro-beta-D-ribo-hexofuranosyl)adenine (4). A second nitroaldol condensation between 4 and N-benzyloxycarbonly-L-aspartic acid-beta-semialdehyde alpha-benzyl ester (5) followed by acetylation and borohydride reduction leads to a fully protected 6'-nitro modification of sinefungin and its C6'-epimer (7). Hydrolysis of the acetonide followed by sequential reduction of the benzyl derived protecting groups and the nitro group and debenzoylation leads to a modest yield of a 3:1 mixture of sinefungin (1) and 6'-episinefungin which can only be separated by analytical ion exchange chromatography.

摘要

N6-苯甲酰基-2',3'-O-异亚丙基腺苷-5'-醛与硝基甲烷缩合，随后进行酸催化乙酰化和硼氢化物还原，得到N6-苯甲酰基-9-(5,6-二脱氧-2,3-O-异亚丙基-6-硝基-β-D-核糖己呋喃糖基)腺嘌呤(4)。4与N-苄氧羰基-L-天冬氨酸-β-半醛α-苄酯(5)之间进行第二次硝基羟醛缩合，随后进行乙酰化和硼氢化物还原，得到西奈芬净及其C6'-差向异构体(7)的完全保护的6'-硝基修饰物。缩丙酮水解，随后依次还原苄基衍生的保护基团和硝基并脱苯甲酰基，得到西奈芬净(1)和6'-表西奈芬净3:1混合物的适中产率，该混合物只能通过分析离子交换色谱法分离。

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本文引用的文献

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Plasmodium falciparum: antimalarial activity in culture of sinefungin and other methylation inhibitors.恶性疟原虫：S-腺苷高半胱氨酸及其他甲基化抑制剂在培养中的抗疟活性
Exp Parasitol. 1980 Aug;50(1):83-9. doi: 10.1016/0014-4894(80)90010-7.
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S-Adenosyl-L-methionine-dependent macromolecule methyltransferases: potential targets for the design of chemotherapeutic agents.S-腺苷-L-甲硫氨酸依赖性大分子甲基转移酶：化疗药物设计的潜在靶点。
J Med Chem. 1980 Apr;23(4):347-57. doi: 10.1021/jm00178a001.
3
Inhibitory activity of sinefungin and SIBA (5'-deoxy-5'-S-isobutylthio-adenosine) on the growth of promastigotes and amastigotes of different species of Leishmania.西奈芬净和SIBA（5'-脱氧-5'-S-异丁硫基腺苷）对不同利什曼原虫物种前鞭毛体和无鞭毛体生长的抑制活性。
FEBS Lett. 1980 Dec 1;121(2):287-91. doi: 10.1016/0014-5793(80)80364-4.
4
Effects of S-adenosylhomocysteine analogues on vaccinia viral messenger ribonucleic acid synthesis and methylation.S-腺苷同型半胱氨酸类似物对痘苗病毒信使核糖核酸合成及甲基化的影响
Biochemistry. 1982 Mar 30;21(7):1535-41. doi: 10.1021/bi00536a011.
5
Reactions of 2-acyloxyisobutyryl halides with nucleosides. II. Reactions of adenosine.2-酰氧基异丁酰卤与核苷的反应。II. 腺苷的反应。
J Am Chem Soc. 1973 Jun 13;95(12):4025-30. doi: 10.1021/ja00793a032.
6
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J Org Chem. 1973 May 18;38(10):1841-5. doi: 10.1021/jo00950a015.
7
A9145, a new adenine-containing antifungal antibiotic: fermentation.A9145，一种新型含腺嘌呤抗真菌抗生素：发酵
Antimicrob Agents Chemother. 1973 Jan;3(1):49-56. doi: 10.1128/AAC.3.1.49.
8
Analogues of S-adenosylhomocysteine as potential inhibitors of biological transmethylation. Synthesis of analogues with modifications at the 5'-thioether linkage.S-腺苷高半胱氨酸类似物作为生物甲基化潜在抑制剂。5'-硫醚键修饰类似物的合成。
J Med Chem. 1976 May;19(5):684-91. doi: 10.1021/jm00227a021.
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