Sporolides

{{Chembox

| ImageFile = Sporolides A and B.jpg

| IUPACName = (3S,7S,8R,12R,17R,19R,21R,25R)-23-chloro-3,12,17,19,21-pentahydroxy-8-methoxy-5-methyl-2,10,24,26-tetraoxaheptacyclo[11.8.2.2^7,7.1^4,18.0^1,18.0^16,22.0^3,25]hexacosa-4,13(23),14,16(22)-tetraene-6,9-dione

| SystematicName =

| Section1 = {{Chembox Identifiers

| index_label = A

| index1_label = B

| ChEBI1 = 219763

| ChEBI2 = 204081

| PubChem = 102352691

| PubChem1 = 76900362

| CASNo =

| ChemSpiderID =

| SMILES = CC1=C2[C@@]3([C@H]4[C@](C1=O)(O4)[C@H](C(=O)OC[C@@H](C5=C(C6=C(C=C5)[C@H](C7(C6(O3)[C@@H](C[C@H]7O)O)O2)O)Cl)O)OC)O

| InChI=1S/C24H23ClO12/c1-7-15(29)21-18(33-2)19(31)34-6-10(26)8-3-4-9-13(14(8)25)22-11(27)5-12(28)23(22,16(9)30)35-17(7)24(32,37-22)20(21)36-21/h3-4,10-12,16,18,20,26-28,30,32H,5-6H2,1-2H3/t10-,11+,12+,16+,18-,20+,21+,22?,23?,24+/m0/s1

| InChI1=1S/C24H23ClO12/c1-7-15(29)21-18(33-2)19(31)34-6-11(26)8-3-9-14(10(25)4-8)16(30)23-13(28)5-12(27)22(9,23)37-24(32,17(7)35-23)20(21)36-21/h3-4,11-13,16,18,20,26-28,30,32H,5-6H2,1-2H3/t11-,12+,13+,16+,18-,20+,21-,22-,23-,24+/m0/s1

| InChIKey = KFIMJAYNUYNRLK-PKIZEOIBSA-N

| InChIKey1 = CYXHIOKLZVVCBQ-LCCPHMJJSA-N

| SMILES1 = CC1=C2C3(C4C(C1=O)(O4)C(C(=O)OCC(C5=CC6=C(C(C7(C6(O3)C(CC7O)O)O2)O)C(=C5)Cl)O)OC)O

}}

| Section2 = {{Chembox Properties

| C=24 | H=23 | Cl=1 | O=12

| MeltingPtC =

}}

}}

Sporolides A and B are polycyclic macrolides extracted from the obligate marine bacterium Salinispora tropica, which is found in ocean sediment. They are composed of a chlorinated cyclopenta[a]indene ring and a cyclohexenone moiety.{{cite journal |doi=10.1021/ja710488m |title=Unraveling the Biosynthesis of the Sporolide Cyclohexenone Building Block |year=2008 |last1=McGlinchey |first1=Ryan P. |last2=Nett |first2=Markus |last3=Moore |first3=Bradley S. |journal=Journal of the American Chemical Society |volume=130 |issue=8 |pages=2406–2407 |pmid=18232689 |bibcode=2008JAChS.130.2406M }} They were the second group of compounds (after salinosporamide A) isolated from Salinispora, and were said to indicate the potential of marine actinomycetes as a source of novel secondary metabolites.{{cite journal |doi=10.1021/ol050901i |title=Sporolides a and b: Structurally Unprecedented Halogenated Macrolides from the Marine Actinomycete Salinisporatropica |year=2005 |last1=Buchanan |first1=Greg O. |last2=Williams |first2=Philip G. |last3=Feling |first3=Robert H. |last4=Kauffman |first4=Christopher A. |last5=Jensen |first5=Paul R. |last6=Fenical |first6=William |journal=Organic Letters |volume=7 |issue=13 |pages=2731–2734 |pmid=15957933 }} The structures and absolute stereochemistries of both metabolites were elucidated using a combination of NMR spectroscopy and X-ray crystallography.

The complex aromatic structure of the sporolides was hypothesized to be derived from an unstable nine-membered ring enediyne precursor, which could undergo Bergman cyclization to generate a para-benzyne intermediate. Nucleophilic attack by chloride would account for the 1:1 mixture of sporolide A and B and for the single chlorine in these enediyne-derived natural products. This proposed mechanism was demonstrated in laboratory experiments,{{cite journal |doi=10.1021/ja070023e |title=Nucleophilic Addition to a p-Benzyne Derived from an Enediyne: A New Mechanism for Halide Incorporation into Biomolecules |year=2007 |last1=Perrin |first1=Charles L. |last2=Rodgers |first2=Betsy L. |last3=O'Connor |first3=Joseph M. |journal=Journal of the American Chemical Society |volume=129 |issue=15 |pages=4795–4799 |pmid=17378569 |bibcode=2007JAChS.129.4795P }}

Image:Nuc.jpg