Brasilinolide B
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| Category | Others |
| Catalog number | BBF-00173 |
| CAS | 262596-89-4 |
| Molecular Weight | 1181.44 |
| Molecular Formula | C59H104O23 |
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Description
Brasilinolide B is a lactone produced by Nocardia brasiliensis.
Specification
| Synonyms | (1R,3R,5R,9S,10S,12S,13R,14R,17E,20S,22R,24S,27R,28R,30S,31R,32S)-14-{(2S,3S,4R,5R,6R,7S)-7-[(2,6-dideoxy-3,4-di-O-methyl-alpha-L-lyxo-hexopyranosyl)oxy]-3,5-dihydroxy-4,6-dimethyloctan-2-yl}-3,9,20,22,24,28,30,31,32-nonahydroxy-13,27-dimethyl-16-oxo-11,15,34-trioxatricyclo[28.3.1.0(10,12)]tetratriacont-17-en-5-yl methyl butylpropanedioate |
| IUPAC Name | 1-O-[(1R,3R,5R,9S,10S,12S,13R,14R,17E,20S,22R,24S,27R,28R,30S,31R,32S)-14-[(2S,3S,4R,5R,6R,7S)-7-[(2R,4S,5R,6S)-4,5-dimethoxy-6-methyloxan-2-yl]oxy-3,5-dihydroxy-4,6-dimethyloctan-2-yl]-3,9,20,22,24,28,30,31,32-nonahydroxy-13,27-dimethyl-16-oxo-11,15,34-trioxatricyclo[28.3.1.010,12]tetratriacont-17-en-5-yl] 3-O-methyl 2-butylpropanedioate |
| Canonical SMILES | CCCCC(C(=O)OC)C(=O)OC1CCCC(C2C(O2)C(C(OC(=O)C=CCC(CC(CC(CCC(C(CC3(C(C(CC(O3)CC(C1)O)O)O)O)O)C)O)O)O)C(C)C(C(C)C(C(C)C(C)OC4CC(C(C(O4)C)OC)OC)O)O)C)O |
| InChI | InChI=1S/C59H104O23/c1-12-13-18-43(57(71)76-11)58(72)79-41-17-15-19-44(64)55-53(81-55)34(6)52(33(5)51(69)32(4)50(68)31(3)35(7)77-49-28-47(74-9)54(75-10)36(8)78-49)80-48(67)20-14-16-37(60)23-39(62)24-38(61)22-21-30(2)46(66)29-59(73)56(70)45(65)27-42(82-59)26-40(63)25-41/h14,20,30-47,49-56,60-66,68-70,73H,12-13,15-19,21-29H2,1-11H3/b20-14+/t30-,31+,32-,33+,34-,35+,36+,37+,38+,39+,40+,41-,42-,43?,44+,45+,46-,47+,49-,50+,51+,52-,53+,54-,55+,56-,59+/m1/s1 |
| InChI Key | AXFOSMASHUQEMX-QWVZVQMISA-N |
Reference Reading
1. Target-specific identification and characterization of the putative gene cluster for brasilinolide biosynthesis revealing the mechanistic insights and combinatorial synthetic utility of 2-deoxy-l-fucose biosynthetic enzymes
Hsien-Tai Chiu, Chien-Pao Weng, Yu-Chin Lin, Kuan-Hung Chen Org Biomol Chem. 2016 Feb 14;14(6):1988-2006. doi: 10.1039/c5ob02292d.
Brasilinolides exhibiting potent immunosuppressive and antifungal activities with remarkably low toxicity are structurally characterized by an unusual modified 2-deoxy-l-fucose (2dF) attached to a type I polyketide (PK-I) macrolactone. From the pathogenic producer Nocardia terpenica (Nocardia brasiliensis IFM-0406), a 210 kb genomic fragment was identified by target-specific degenerate primers and subsequently sequenced, revealing a giant nbr gene cluster harboring genes (nbrCDEF) required for TDP-2dF biosynthesis and those for PK-I biosynthesis, modification and regulation. The results showed that the genetic and domain arrangements of nbr PK-I synthases agreed colinearly with the PK-I structures of brasilinolides. Subsequent heterologous expression of nbrCDEF in Escherichia coli accomplished in vitro reconstitution of TDP-2dF biosynthesis. The catalytic functions and mechanisms of NbrCDEF enzymes were further characterized by systematic mix-and-match experiments. The enzymes were revealed to display remarkable substrate and partner promiscuity, leading to the establishment of in vitro hybrid deoxysugar biosynthetic pathways throughout an in situ one-pot (iSOP) method. This study represents the first demonstration of TDP-2dF biosynthesis at the enzyme and molecular levels, and provides new hope for expanding the structural diversity of brasilinolides by combinatorial biosynthesis.
2. Toward the total synthesis of the brasilinolides: construction of a differentially protected C20-C38 segment
Ian Paterson, Paul M Burton, Christopher J Cordier, Michael P Housden, Friedrich A Mühlthau, Olivier Loiseleur Org Lett. 2009 Feb 5;11(3):693-6. doi: 10.1021/ol802769e.
An efficient, convergent synthesis of a differentially protected C20-C38 segment of the brasilinolides is described. Iterative 1,4-syn aldol additions and ketone reductions were employed to construct the two related stereotetrads, while a sequence of Horner-Wadsworth-Emmons (HWE) coupling, CBS reduction, and Sharpless AE installed the epoxy alcohol functionality.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
