| 词条 | Palau'amine |
| 释义 |
| ImageFile = Palau amine.svg | ImageFile_Ref = {{chemboximage|correct|??}} | ImageName = Chemical structure of palau'amine | SystematicName = 2,2'-Diamino-11-(aminomethyl)-12-chloro-1,1',3a,5',10a,11,12,13a-octahydro-5'-hydroxy-spiro[8H-cyclopenta[3,4]pyrrolo[1,2-a]imidazo[4,5-b]pyrrolo[1,2-d]pyrazine-13(10H),4'-[4H]imidazol]-8-one[1] |Section1={{Chembox Identifiers | CASNo = 148717-58-2 | SMILES = Cl[C@@H]4[C@@]1(NC(=N/[C@H]1O)\)[C@H]3[C@@]26/N=C(\[C@H]6n5c(C(=O)N2C[C@@H]3[C@H]4CN)ccc5)N | InChI = 1/C17H22ClN9O2/c18-10-6(4-19)7-5-27-11(28)8-2-1-3-26(8)12-17(27,25-14(20)22-12)9(7)16(10)13(29)23-15(21)24-16/h1-3,6-7,9-10,12-13,29H,4-5,19H2,(H3,20,22,25)(H3,21,23,24)/t6-,7-,9+,10+,12+,13+,16+,17-/m1/s1 | InChIKey = VYOQBYCIIJYKJA-VORKOXQSBL | StdInChI = 1S/C17H22ClN9O2/c18-10-6(4-19)7-5-27-11(28)8-2-1-3-26(8)12-17(27,25-14(20)22-12)9(7)16(10)13(29)23-15(21)24-16/h1-3,6-7,9-10,12-13,29H,4-5,19H2,(H3,20,22,25)(H3,21,23,24)/t6-,7-,9+,10+,12+,13+,16+,17-/m1/s1 | StdInChIKey = VYOQBYCIIJYKJA-VORKOXQSSA-N | MeSHName = C438976 | PubChem = 16122048 | ChemSpiderID = 17279008 | ChEMBL = 2079438 }} |Section2={{Chembox Properties | C=17 | H=22 | N=9 | O=2 | Cl=1 }} }} Palau'amine is a toxic alkaloid compound synthesized naturally by Stylotella agminata, a species of sea sponge found in the southwest Pacific Ocean. The name of the molecule derives from the island nation of Palau, near which the sponges are found. The substance was first isolated and described in 1993.[2] Containing nine nitrogen atoms, the molecule is considered highly complex. The precise atomic structure was pinned down in 2007,[3] and two years later the molecule was synthesized in the lab of Phil Baran at the Scripps Research Institute in La Jolla, California.[4][5] Early efforts towards its synthesis were directed at a misassigned structure featuring a cis- rather than trans-5/5 ring fusion, an error that was made because the trans-5/5 ring system is some 6 kcal/mol less stable than the cis-configured system.[6] Biomimetic synthesisBased on the hypothesized biosynthesis of palau'amine, a proposed pathway to this dimeric pyrrole-imidazole alkaloid includes a key oxidation of a β-ketoester with manganese(III) acetate to initiate a cascade radical cyclization, producing an ageliferin skeleton.[7] Biological effectsPalau'amine is a proteasome inhibitor.[8] References1. ^Chemical Abstracts, accessed via SciFinder, version 2004.2; Chemical Abstracts Service: Columbus, OH, 2004; RN 148717-58-2 2. ^{{cite journal | title =Palau'amine: a cytotoxic and immunosuppressive hexacyclic bisguanidine antibiotic from the sponge Stylotella agminata | first1 =Robin B. | last1 = Kinnel| first2 = Henning Peter | last2 = Gehrken | first3 =Paul J. | last3 = Scheuer | journal = Journal of the American Chemical Society | year = 1993 | volume = 115 | issue = 8 | pages = 3376–3377 | doi = 10.1021/ja00061a065}} 3. ^{{cite journal | journal = Chemical & Engineering News| year = 2007 | volume = 85 | issue = 10 | page = 12| title = Sponge Alkaloids: Palau'amine Reconsidered | first =Bethany | last = Halford | url =http://pubs.acs.org/cen/news/85/i10/8510notw7.html | doi=10.1021/cen-v085n010.p012a}} 4. ^{{cite journal | doi = 10.1002/anie.200907112 | pmid =20041464 | journal =Angewandte Chemie International Edition | title = Total Synthesis of Palau'amine| first1 = Ian B. | last1 = Seiple | first2 = Shun | last2 = Su | first3 = Ian S. | volume = 49 | issue =6 | last3 = Young | first4 = Chad A. | last4 = Lewis | first5 = Junichiro | pages = 1095–8 | last5 = Yamaguchi | first6 = Phil S.| last6 = Baran | authorlink6 = Phil S. Baran | year = 2010| pmc = 3367661 }} 5. ^{{cite journal | first = Alexis | last = Madrigal | date = 2010-01-14 | title = Bizarre Sea Sponge Compound Finally Synthesized by Humans | journal = Wired | url = https://www.wired.com/wiredscience/2010/01/palauamine-synthesized/ | accessdate = 2010-01-15}} 6. ^{{Cite journal|last=Usami|first=Yoshihide|date=2009-07-13|title=Recent Synthetic Studies Leading to Structural Revisions of Marine Natural Products|journal=Marine Drugs|volume=7|issue=3|pages=314–330|doi=10.3390/md7030314|issn=1660-3397|pmc=2763102|pmid=19841716}} 7. ^{{cite journal |journal=Chem Commun| date= Jan 7, 2011|volume=47|issue=1|pages=427–9| title=Revisiting the Kinnel–Scheuer hypothesis for the biosynthesis of palau'amine |vauthors=Ma Z, Lu J, Wang X, Chen C | pmid= 20848010| doi=10.1039/c0cc02214d| pmc=2999656}} 8. ^{{cite journal|title=Palau'amine and Related Oroidin-alkaloids Dibromophakellin and Dibromophakellstatin Inhibit the Human 20S Proteasome|journal=Journal of Natural Products|volume=75|issue=5|pages=980–5|doi=10.1021/np300231f|pmid=22591513|pmc=3367325|year=2012|author1=Lansdell|first1=T. A|last2=Hewlett|first2=N. M|last3=Skoumbourdis|first3=A. P|last4=Fodor|first4=M. D|last5=Seiple|first5=I. B|last6=Su|first6=S|last7=Baran|first7=P. S|last8=Feldman|first8=K. S|last9=Tepe|first9=J. J}} 8 : Alkaloids|Organochlorides|Halogen-containing alkaloids|Guanidine alkaloids|Amines|Spiro compounds|Nitrogen heterocycles|Proteasome inhibitors |
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