天然产物结构修饰的最新趋势。
Recent trends in the structural revision of natural products.
机构信息
School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 30332, USA.
出版信息
Nat Prod Rep. 2018 Jun 20;35(6):514-531. doi: 10.1039/c8np00011e.
Abstract
Covering: 2012 to 2017 This article reviews recent reports on the structural revision of natural products. Through a critical assessment of the original and revised published structures, the article addresses why each structure was targeted for revision, discusses the techniques and key discrepancies that led to the proposal of the revised structure, and offers measures that may have been taken during the original structure determination to prevent error. With the revised structures in hand, weaknesses of original proposals are assessed, providing a better understanding on the logic behind structure determination.
摘要
涵盖时间
2012 年至 2017 年
本文综述了近年来关于天然产物结构修订的报道。通过对原始和修订后发表结构的批判性评估，本文探讨了每个结构被修订的原因，讨论了导致提出修订结构的技术和关键差异，并提出了在原始结构测定过程中可能采取的防止错误的措施。掌握了修订后的结构后，评估了原始建议的弱点，从而更好地理解结构测定背后的逻辑。
相似文献
1
Recent trends in the structural revision of natural products.天然产物结构修饰的最新趋势。
Nat Prod Rep. 2018 Jun 20;35(6):514-531. doi: 10.1039/c8np00011e.
2
Revised structure, total synthesis, and absolute configuration of kopeolin and kopeolone.科佩奥林和科佩奥酮的结构修订、全合成及绝对构型
J Org Chem. 2014 Mar 7;79(5):2268-73. doi: 10.1021/jo402572b. Epub 2014 Feb 17.
3
Synthesis-guided structure revision of the sarcodonin, sarcoviolin, and hydnellin natural product family.基于合成指导的肌蛤菌素、石耳菌素和齿孔菌素天然产物家族的结构修正。
J Org Chem. 2011 Feb 18;76(4):1013-30. doi: 10.1021/jo102228j. Epub 2011 Jan 20.
4
Computational Structural Revision of Elaeophorbate and Other Triterpenoids with the Help of NAPROC-13. A New Strategy for Structural Revision of Natural Products.借助NAPROC-13对油叶菌素及其他三萜类化合物进行计算结构修正。一种天然产物结构修正的新策略。
J Nat Prod. 2023 Apr 28;86(4):897-908. doi: 10.1021/acs.jnatprod.2c01135. Epub 2023 Mar 7.
5
Total synthesis of a diastereomer of the marine natural product clavosolide A.海洋天然产物克拉沃索利德A非对映异构体的全合成。
Chem Commun (Camb). 2005 Oct 28(40):5097-9. doi: 10.1039/b509757f. Epub 2005 Sep 15.
6
Structural Revisions of a Class of Natural Products: Scaffolds of Aglycon Analogues of Fusicoccins and Cotylenins Isolated from Fungi.一类天然产物的结构修订：从真菌中分离出的壳梭孢菌素和杯体菌素苷元类似物的支架结构
Angew Chem Int Ed Engl. 2016 Mar 14;55(12):4069-73. doi: 10.1002/anie.201600313. Epub 2016 Feb 24.
7
Synthesis and Stereochemical Revision of the C31-C67 Fragment of Amphidinol 3.合成与立体化学修订 Amphidinol 3 的 C31-C67 片段。
Angew Chem Int Ed Engl. 2018 May 22;57(21):6060-6064. doi: 10.1002/anie.201712167. Epub 2018 Apr 27.
8
Structural reassignment of a marine metabolite from a binaphthalenetetrol to a tetrabrominated diphenyl ether.从联萘酚四醇到四溴二苯醚的海洋代谢产物的结构重分配。
J Nat Prod. 2012 Jun 22;75(6):1125-9. doi: 10.1021/np300141t. Epub 2012 Jun 12.
9
Determination of absolute configuration using single crystal X-ray diffraction.使用单晶X射线衍射确定绝对构型。
Methods Mol Biol. 2013;1055:149-62. doi: 10.1007/978-1-62703-577-4_11.
10
Chemoenzymatic total syntheses of ribisins A, B, and D, polyoxygenated benzofuran derivatives displaying NGF-potentiating properties.核糖菌素A、B和D的化学酶法全合成，具有多氧取代的苯并呋喃衍生物，展现出增强神经生长因子（NGF）的特性。
J Org Chem. 2014 Apr 4;79(7):2829-42. doi: 10.1021/jo500210k. Epub 2014 Feb 28.
引用本文的文献
1
Elucidating Structures of Complex Organic Compounds Using a Machine Learning Model Based on the C NMR Chemical Shifts.使用基于碳核磁共振化学位移的机器学习模型解析复杂有机化合物的结构
Precis Chem. 2023 Feb 15;1(1):57-68. doi: 10.1021/prechem.3c00005. eCollection 2023 Mar 27.
2
Synergy of Prediction Rule and Total Synthesis in Solving the Stereochemical Puzzle of Valactamides.预测规则与全合成在解决戊内酰胺立体化学难题中的协同作用。
Precis Chem. 2024 Jan 23;2(3):120-126. doi: 10.1021/prechem.3c00109. eCollection 2024 Mar 25.
3
Total Synthesis of the Norcembranoid Scabrolide B and Its Transformation into Sinuscalide C, Ineleganolide, and Horiolide.降蒈二烯类化合物Scabrolide B的全合成及其向Sinuscalide C、Ineleganolide和Horiolide的转化
J Am Chem Soc. 2024 Sep 4;146(35):24250-24256. doi: 10.1021/jacs.4c09467. Epub 2024 Aug 21.
4
Total Syntheses and Stereochemical Assignment of Acremolides A and B.顶头孢菌素A和B的全合成及立体化学归属
Molecules. 2024 Jul 30;29(15):3599. doi: 10.3390/molecules29153599.
5
Polyoxygenated cembrane-type diterpenes from the Hainan soft coral Lobophytum crassum as a promising source of anticancer agents with ErbB3 and ROR1 inhibitory potential.来自海南软珊瑚厚叶扁柳珊瑚的多氧化西松烷型二萜类化合物作为具有ErbB3和ROR1抑制潜力的抗癌剂的潜在来源。
Acta Pharmacol Sin. 2025 Jan;46(1):196-207. doi: 10.1038/s41401-024-01347-z. Epub 2024 Jul 29.
6
Structure Revision of Formyl Phloroglucinol Meroterpenoids: A Unified Approach Using NMR Fingerprinting and DFT NMR and ECD Analyses.间苯三酚甲醛缩合萜类化合物的结构修订：一种结合核磁共振指纹图谱、密度泛函理论核磁共振及电子圆二色光谱分析的统一方法
Molecules. 2024 Jan 25;29(3):594. doi: 10.3390/molecules29030594.
7
High-Throughput Identification of Crystalline Natural Products from Crude Extracts Enabled by Microarray Technology and microED.通过微阵列技术和微电子衍射实现的粗提物中结晶天然产物的高通量鉴定
ACS Cent Sci. 2023 Dec 20;10(1):176-183. doi: 10.1021/acscentsci.3c01365. eCollection 2024 Jan 24.
8
The Synergy between Nuclear Magnetic Resonance and Density Functional Theory Calculations.核磁共振与密度泛函理论计算之间的协同作用。
Molecules. 2024 Jan 9;29(2):336. doi: 10.3390/molecules29020336.
9
OSMAC Approach and Cocultivation for the Induction of Secondary Metabolism of the Fungus .用于诱导真菌次级代谢的OSMAC方法与共培养
ACS Omega. 2023 Oct 16;8(42):39873-39885. doi: 10.1021/acsomega.3c06299. eCollection 2023 Oct 24.
10
Identification of a Family of Glycoside Derivatives Biologically Active against and Other MDR Bacteria Using a QSPR Model.使用定量构效关系（QSPR）模型鉴定对[具体细菌名称]和其他多重耐药菌具有生物活性的糖苷衍生物家族。 （你原文中“against”后面缺少具体细菌名称，我按格式补全了，实际翻译时请根据准确内容调整）
Pharmaceuticals (Basel). 2023 Feb 7;16(2):250. doi: 10.3390/ph16020250.
本文引用的文献
1
Structure Revision of Poecillastrin C and the Absolute Configuration of the β-Hydroxyaspartic Acid Residue.Poecillastrin C 的结构修订及 β-羟基天冬氨酸残基的绝对构型。
Org Lett. 2017 Oct 6;19(19):5395-5397. doi: 10.1021/acs.orglett.7b02835. Epub 2017 Sep 28.
2
The importance of asking "how and why?" in natural product structure elucidation.在天然产物结构阐明中提出“如何”和“为什么”的重要性。
Nat Prod Rep. 2017 Oct 18;34(10):1193-1202. doi: 10.1039/c7np00025a.
3
Cycloelatanene A and B: absolute configuration determination and structural revision by the crystalline sponge method.环拉他烯A和B：通过晶体海绵法确定绝对构型并进行结构修正
Chem Sci. 2017 Feb 1;8(2):1547-1550. doi: 10.1039/c6sc04288k. Epub 2016 Oct 27.
4
Structural Revision and Biosynthesis of the Fungal Phytotoxins Phyllostictines A and B.真菌植物毒素叶点霉素A和B的结构修正与生物合成
J Nat Prod. 2017 May 26;80(5):1235-1240. doi: 10.1021/acs.jnatprod.7b00183. Epub 2017 May 3.
5
Structural Reassignment and Absolute Stereochemistry of Madurastatin C1 (MBJ-0034) and the Related Aziridine Siderophores: Madurastatins A1, B1, and MBJ-0035.马杜拉他汀C1（MBJ - 0034）及相关氮丙啶铁载体：马杜拉他汀A1、B1和MBJ - 0035的结构重新分配与绝对立体化学
J Nat Prod. 2017 May 26;80(5):1558-1562. doi: 10.1021/acs.jnatprod.7b00082. Epub 2017 Apr 11.
6
Unequivocal determination of complex molecular structures using anisotropic NMR measurements.使用各向异性核磁共振测量对复杂分子结构进行明确测定。
Science. 2017 Apr 7;356(6333). doi: 10.1126/science.aam5349.
7
High-Throughput in Silico Structure Validation and Revision of Halogenated Natural Products Is Enabled by Parametric Corrections to DFT-Computed C NMR Chemical Shifts and Spin-Spin Coupling Constants.基于参数修正的 DFT 计算 13C NMR 化学位移和自旋-自旋偶合常数实现了卤代天然产物的高通量计算结构验证和修正。
J Org Chem. 2017 Apr 7;82(7):3368-3381. doi: 10.1021/acs.joc.7b00188. Epub 2017 Mar 24.
8
Reassignment of the absolute configuration of plakinidone from the sponge consortium using a combination of synthesis and a chiroptical approach.结合合成方法和手性光学方法重新确定来自海绵共生体的普拉基多酮的绝对构型。
Tetrahedron Asymmetry. 2016 Jun;27(9-10):410-419. doi: 10.1016/j.tetasy.2016.03.011. Epub 2016 Apr 7.
9
Skeleton Reassignment of Type C Polycyclic Polyprenylated Acylphloroglucinols.C型多环多异戊烯基化酰基间苯三酚的骨架重新分配
J Nat Prod. 2017 Jan 27;80(1):108-113. doi: 10.1021/acs.jnatprod.6b00754. Epub 2016 Dec 29.
10
Spoxazomicin D and Oxachelin C, Potent Neuroprotective Carboxamides from the Appalachian Coal Fire-Associated Isolate Streptomyces sp. RM-14-6.斯波沙唑霉素D和奥沙西林C，来自阿巴拉契亚煤火相关菌株链霉菌RM-14-6的强效神经保护羧酰胺。
J Nat Prod. 2017 Jan 27;80(1):2-11. doi: 10.1021/acs.jnatprod.6b00948. Epub 2016 Dec 28.
Zotero 插件