萨尔瓦地腺苷，一种来自巴哈马被囊动物Didemnum sp.的5'-脱氧-5'-(甲硫基)核苷。
Salvadenosine, a 5'-deoxy-5'-(methylthio) nucleoside from the Bahamian tunicate Didemnum sp.
作者信息
Jamison Matthew T, Boddy Christopher N, Molinski Tadeusz F
机构信息
Department of Chemistry and Biochemistry and Skaggs School of Pharmacy and §Department of Pharmaceutical Sciences, University of California, San Diego , La Jolla, California 92093-0358, United States.
出版信息
J Org Chem. 2014 Nov 7;79(21):9992-7. doi: 10.1021/jo501486p. Epub 2014 Oct 20.
Abstract
Salvadenosine, (1) a rare 5'-deoxy-5'-(methylthio) nucleoside, was isolated from the deep-water Bahaman tunicate Didemnum sp. The structure was solved by integrated analysis of MS and 1D and 2D NMR data. We revise the structure of the known natural product, hamiguanosinol, which is a constitutional isomer of 1, to 5 by interpretation of the spectroscopic data and comparison with synthesized nucleosides.
摘要
萨尔瓦地腺苷（1）是一种罕见的5'-脱氧-5'-（甲硫基）核苷，从巴哈马深海被囊动物Didemnum sp.中分离得到。通过对质谱以及一维和二维核磁共振数据的综合分析确定了其结构。通过对光谱数据的解读并与合成核苷进行比较，我们将已知天然产物哈米胍醇（它是1的构造异构体）的结构修正为5。
相似文献
1
Salvadenosine, a 5'-deoxy-5'-(methylthio) nucleoside from the Bahamian tunicate Didemnum sp.
J Org Chem. 2014 Nov 7;79(21):9992-7. doi: 10.1021/jo501486p. Epub 2014 Oct 20.
2
Lepadins I-K, 3- O-(3'-Methylthio)acryloyloxy-decahydroquinoline Esters from a Bahamian Ascidian Didemnum sp. Assignment of Absolute Stereostructures.
J Org Chem. 2018 Nov 16;83(22):13670-13677. doi: 10.1021/acs.joc.8b01609. Epub 2018 Oct 26.
3
Tubercidin analogs from the ascidian Didemnum voeltzkowi.
J Nat Prod. 1996 Oct;59(10):1000-1. doi: 10.1021/np960457f.
4
Antibacterial Bicyclic Fatty Acids from a Korean Colonial Tunicate sp.
Mar Drugs. 2021 Sep 16;19(9):521. doi: 10.3390/md19090521.
5
Synthesis, structure revision, and absolute configuration of (+)-didemniserinolipid B, a serinol marine natural product from a tunicate Didemnum sp.
Org Lett. 2002 Sep 19;4(19):3223-6. doi: 10.1021/ol026421y.
6
Epimeric methylsulfinyladenosine derivatives from the marine ascidian Herdmania momus.
Bioorg Med Chem Lett. 2013 Aug 15;23(16):4701-4. doi: 10.1016/j.bmcl.2013.05.097. Epub 2013 Jun 7.
7
Didemnacerides A and B: two new glycerides from Red Sea ascidian Didemnum species.
Nat Prod Res. 2014;28(19):1591-7. doi: 10.1080/14786419.2014.927874. Epub 2014 Jun 18.
8
Total synthesis and absolute configuration of minalemine A, a guanidine peptide from the marine tunicate Didemnum rodriguesi.
J Org Chem. 2001 Jun 15;66(12):4206-13. doi: 10.1021/jo010076t.
9
3,7-Isoquinoline quinones from the ascidian tunicate Ascidia virginea.
Z Naturforsch C J Biosci. 2017 Jul 14;72(7-8):259-264. doi: 10.1515/znc-2017-0012.
10
Diverse Aromatic Metabolites in the Solitary Tunicate .
J Nat Prod. 2020 Oct 23;83(10):3156-3165. doi: 10.1021/acs.jnatprod.0c00789. Epub 2020 Oct 8.
引用本文的文献
1
Secondary Metabolites of the Genus : A Comprehensive Review of Chemical Diversity and Pharmacological Properties.
Mar Drugs. 2020 Jun 11;18(6):307. doi: 10.3390/md18060307.
2
Marine Alkylpurines: A Promising Group of Bioactive Marine Natural Products.
Mar Drugs. 2018 Jan 1;16(1):6. doi: 10.3390/md16010006.
本文引用的文献
1
Acremolin from Acremonium strictum is N(2),3-etheno-2'-isopropyl-1-methylguanine, not a 1H-azirine. Synthesis and structural revision.
Org Lett. 2013 May 17;15(10):2370-3. doi: 10.1021/ol400752s. Epub 2013 May 1.
2
Methionine salvage and S-adenosylmethionine: essential links between sulfur, ethylene and polyamine biosynthesis.
Biochem J. 2013 Apr 15;451(2):145-54. doi: 10.1042/BJ20121744.
3
Bromination at C-5 of Pyrimidine and C-8 of Purine Nucleosides with 1,3-Dibromo-5,5-dimethylhydantoin.
Tetrahedron Lett. 2012 Jun 27;53(26):3333-3336. doi: 10.1016/j.tetlet.2012.04.081. Epub 2012 Apr 24.
4
NMR of natural products at the 'nanomole-scale'.
Nat Prod Rep. 2010 Mar;27(3):321-9. doi: 10.1039/b920545b. Epub 2010 Feb 8.
5
NMR quantitation of natural products at the nanomole scale.
J Nat Prod. 2009 Apr;72(4):739-44. doi: 10.1021/np900009b.
6
Nanomole-scale natural products discovery.
Curr Opin Drug Discov Devel. 2009 Mar;12(2):197-206.
7
S-adenosyl-L-methionine:hydroxide adenosyltransferase: a SAM enzyme.
Angew Chem Int Ed Engl. 2008;47(29):5357-61. doi: 10.1002/anie.200800794.
8
Discovery and characterization of a marine bacterial SAM-dependent chlorinase.
Nat Chem Biol. 2008 Jan;4(1):69-74. doi: 10.1038/nchembio.2007.56. Epub 2007 Dec 2.
9
Highly polar spiroisoxazolines from the sponge Aplysina fulva.
J Nat Prod. 2007 Jul;70(7):1191-4. doi: 10.1021/np070109l. Epub 2007 Jun 19.
10
Spermine participates in oxidative damage of guanosine and 8-oxoguanosine leading to deoxyribosylurea formation.
J Am Chem Soc. 2004 Aug 11;126(31):9540-1. doi: 10.1021/ja047981q.
Zotero 插件