دورية أكاديمية

Approaches to Configuration Determinations of Flexible Marine Natural Products: Advances and Prospects.

التفاصيل البيبلوغرافية
العنوان: Approaches to Configuration Determinations of Flexible Marine Natural Products: Advances and Prospects.
المؤلفون: Huo ZQ; State Key Laboratory of Generic Manufacture Technology of Chinese Traditional Medicine, Lunan Pharmaceutical Group Co., Ltd., Linyi 273400, China., Zhu F; State Key Laboratory of Generic Manufacture Technology of Chinese Traditional Medicine, Lunan Pharmaceutical Group Co., Ltd., Linyi 273400, China., Zhang XW; State Key Laboratory of Microbial Technology, Shandong University, Qingdao 266237, China., Zhang X; College of Pharmacy, Shandong University of Traditional Chinese Medicine, Jinan 250355, China., Liang HB; State Key Laboratory of Generic Manufacture Technology of Chinese Traditional Medicine, Lunan Pharmaceutical Group Co., Ltd., Linyi 273400, China.; College of Pharmacy, Shandong University of Traditional Chinese Medicine, Jinan 250355, China., Yao JC; State Key Laboratory of Generic Manufacture Technology of Chinese Traditional Medicine, Lunan Pharmaceutical Group Co., Ltd., Linyi 273400, China., Liu Z; State Key Laboratory of Generic Manufacture Technology of Chinese Traditional Medicine, Lunan Pharmaceutical Group Co., Ltd., Linyi 273400, China., Zhang GM; State Key Laboratory of Generic Manufacture Technology of Chinese Traditional Medicine, Lunan Pharmaceutical Group Co., Ltd., Linyi 273400, China.; College of Pharmacy, Shandong University of Traditional Chinese Medicine, Jinan 250355, China., Yao QQ; Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250000, China., Qin GF; State Key Laboratory of Generic Manufacture Technology of Chinese Traditional Medicine, Lunan Pharmaceutical Group Co., Ltd., Linyi 273400, China.
المصدر: Marine drugs [Mar Drugs] 2022 May 19; Vol. 20 (5). Date of Electronic Publication: 2022 May 19.
نوع المنشور: Journal Article; Review
اللغة: English
بيانات الدورية: Publisher: MDPI Country of Publication: Switzerland NLM ID: 101213729 Publication Model: Electronic Cited Medium: Internet ISSN: 1660-3397 (Electronic) Linking ISSN: 16603397 NLM ISO Abbreviation: Mar Drugs Subsets: MEDLINE
أسماء مطبوعة: Original Publication: Basel, Switzerland : MDPI, [2003]-
مواضيع طبية MeSH: Biological Products*/chemistry, Circular Dichroism ; Crystallography, X-Ray ; Magnetic Resonance Spectroscopy ; Molecular Structure
مستخلص: Flexible marine natural products (MNPs), such as eribulin and bryostatin, play an important role in the development of modern marine drugs. However, due to the multiple chiral centers and geometrical uncertainty of flexible systems, configuration determinations of flexible MNPs face great challenges, which, in turn, have led to obstacles in druggability research. To resolve this issue, the comprehensive use of multiple methods is necessary. Additionally, configuration assignment methods, such as X-ray single-crystal diffraction (crystalline derivatives, crystallization chaperones, and crystalline sponges), NMR-based methods (JBCA and Mosher's method), circular dichroism-based methods (ECCD and ICD), quantum computational chemistry-based methods (NMR calculations, ECD calculations, and VCD calculations), and chemical transformation-based methods should be summarized. This paper reviews the basic principles, characteristics, and applicability of the methods mentioned above as well as application examples to broaden the research and applications of these methods and to provide a reference for the configuration determinations of flexible MNPs.
References: J Org Chem. 2015 Dec 18;80(24):12526-34. (PMID: 26580165)
Angew Chem Int Ed Engl. 2020 Sep 7;59(37):15875-15879. (PMID: 32441841)
Angew Chem Int Ed Engl. 2011 Sep 26;50(40):9487-90. (PMID: 21915963)
J Nat Prod. 2017 Sep 22;80(9):2551-2555. (PMID: 28840714)
J Org Chem. 2018 Jan 5;83(1):194-202. (PMID: 29185743)
Org Lett. 2020 Jan 3;22(1):52-56. (PMID: 31833778)
J Org Chem. 2015 Aug 21;80(16):7849-55. (PMID: 26222145)
Chirality. 2016 Jun;28(6):466-74. (PMID: 27098594)
J Am Chem Soc. 2008 Oct 29;130(43):14234-43. (PMID: 18826315)
Acta Crystallogr D Biol Crystallogr. 2015 Apr;71(Pt 4):896-906. (PMID: 25849400)
Angew Chem Int Ed Engl. 2021 Nov 22;60(48):25204-25222. (PMID: 34109717)
J Nat Prod. 2019 Aug 23;82(8):2299-2306. (PMID: 31322872)
Chemistry. 2002 Jul 15;8(14):3233-9. (PMID: 12203353)
J Org Chem. 2001 Jul 13;66(14):4819-25. (PMID: 11442411)
J Nat Prod. 2016 Apr 22;79(4):1144-8. (PMID: 27064611)
ACS Chem Biol. 2017 Aug 18;12(8):2157-2163. (PMID: 28617580)
Chirality. 2008 May 15;20(5):643-63. (PMID: 17955495)
J Am Chem Soc. 2020 Feb 5;142(5):2301-2309. (PMID: 31889437)
J Nat Prod. 2007 Oct;70(10):1672-5. (PMID: 17929896)
Nat Prod Rep. 2022 Jan 26;39(1):58-76. (PMID: 34212963)
Org Biomol Chem. 2012 Jun 7;10(21):4208-14. (PMID: 22543980)
Curr Med Chem. 2018;25(2):287-320. (PMID: 28294053)
J Am Chem Soc. 2010 Sep 22;132(37):12946-59. (PMID: 20795713)
Chirality. 2001 Jun;13(6):313-21. (PMID: 11370021)
Org Biomol Chem. 2013 Aug 7;11(29):4847-59. (PMID: 23779148)
J Org Chem. 2018 Nov 2;83(21):13256-13266. (PMID: 30280904)
J Nat Prod. 2020 Apr 24;83(4):1314-1333. (PMID: 32091208)
Chem Commun (Camb). 2009 Oct 28;(40):5958-80. (PMID: 19809616)
Chirality. 2022 Feb;34(2):333-363. (PMID: 34791704)
Nat Prod Rep. 2019 Jul 1;36(7):1005-1030. (PMID: 31166350)
Chem Commun (Camb). 2018 Mar 27;54(26):3247-3250. (PMID: 29536067)
Chemistry. 2001 Apr 17;7(8):1652-61. (PMID: 11349906)
J Org Chem. 2015 Oct 2;80(19):9371-8. (PMID: 26339863)
Chirality. 2008 May 15;20(5):681-90. (PMID: 17924422)
Chemistry. 2014 Dec 22;20(52):17385-94. (PMID: 25346258)
Nat Prod Rep. 2014 Jan 17;31(2):160-258. (PMID: 24389707)
Nat Protoc. 2007;2(10):2451-8. (PMID: 17947986)
Chirality. 2022 Feb;34(2):163-181. (PMID: 34766388)
Science. 2017 Apr 7;356(6333):. (PMID: 28385960)
Arch Pharm Res. 2020 Nov;43(11):1114-1127. (PMID: 33123961)
Nature. 2013 Mar 28;495(7442):461-6. (PMID: 23538828)
Mar Drugs. 2015 Apr 29;13(5):2694-713. (PMID: 25939037)
Angew Chem Int Ed Engl. 2016 Feb 18;55(8):2678-82. (PMID: 26880368)
Org Biomol Chem. 2016 Apr 28;14(16):3943-9. (PMID: 27045792)
ACS Cent Sci. 2018 Nov 28;4(11):1587-1592. (PMID: 30555912)
Chem Sci. 2020 Mar 6;11(17):4351-4359. (PMID: 34122893)
Mar Drugs. 2021 Dec 22;20(1):. (PMID: 35049868)
Nat Prod Rep. 2021 Mar 4;38(2):362-413. (PMID: 33570537)
Nat Prod Rep. 2019 Jun 19;36(6):889-918. (PMID: 31139804)
J Org Chem. 2007 Apr 13;72(8):2906-16. (PMID: 17375957)
Org Biomol Chem. 2006 Jun 7;4(11):2233-40. (PMID: 16729132)
Chem Sci. 2019 Jul 29;10(38):8774-8791. (PMID: 31803450)
Org Lett. 2019 Dec 20;21(24):10125-10129. (PMID: 31820648)
J Org Chem. 2006 Aug 4;71(16):6074-98. (PMID: 16872191)
J Nat Prod. 2019 Dec 27;82(12):3440-3449. (PMID: 31799843)
Nat Prod Bioprospect. 2018 Aug;8(4):279-295. (PMID: 29943349)
Bioorg Med Chem. 2021 Apr 1;35:116058. (PMID: 33588288)
Chem Rev. 2007 Sep;107(9):3744-79. (PMID: 17649982)
Org Lett. 2002 Aug 8;4(16):2779-82. (PMID: 12153233)
Biomolecules. 2022 Mar 09;12(3):. (PMID: 35327613)
J Org Chem. 1999 Feb 5;64(3):866-876. (PMID: 11674159)
J Nat Prod. 2020 Apr 24;83(4):1061-1068. (PMID: 32091903)
J Chem Inf Comput Sci. 2002 Mar-Apr;42(2):241-8. (PMID: 11911693)
Chirality. 2009;21 Suppl 1:E181-201. (PMID: 19902530)
J Am Chem Soc. 2005 Jul 6;127(26):9561-70. (PMID: 15984883)
Nat Protoc. 2019 Jan;14(1):217-247. (PMID: 30552410)
Life (Basel). 2021 Dec 11;11(12):. (PMID: 34947921)
Angew Chem Int Ed Engl. 2018 May 22;57(21):6060-6064. (PMID: 29635773)
Chem Commun (Camb). 2016 Mar 28;52(25):4632-5. (PMID: 26948938)
Chem Soc Rev. 2013 Jun 21;42(12):5408-24. (PMID: 23482984)
Tetrahedron. 2012 Nov 18;68(46):9307-9343. (PMID: 23814320)
Org Lett. 2019 Jun 7;21(11):4003-4007. (PMID: 31124687)
Chem Rev. 2012 Mar 14;112(3):1839-62. (PMID: 22091891)
معلومات مُعتمدة: 32000039 National Natural Science Foundation of China; 2021CXGC010508 Shandong Provincial Key Research and Development Program (Major Technological Innovation Project); 2019ZDZX001 Independent Innovation Major Project of Linyi City, Shandong Province
فهرسة مساهمة: Keywords: NMR-based methods; X-ray single-crystal diffraction; chemical transformation-based methods; circular dichroism-based methods; configuration determinations; flexible marine natural products; quantum computational chemistry-based methods
المشرفين على المادة: 0 (Biological Products)
تواريخ الأحداث: Date Created: 20220527 Date Completed: 20220531 Latest Revision: 20220716
رمز التحديث: 20231215
مُعرف محوري في PubMed: PMC9143581
DOI: 10.3390/md20050333
PMID: 35621984
قاعدة البيانات: MEDLINE
الوصف
تدمد:1660-3397
DOI:10.3390/md20050333