Brasilinolide A
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| Category | Antibiotics |
| Catalog number | BBF-00172 |
| CAS | 179041-27-1 |
| Molecular Weight | 1167.37 |
| Molecular Formula | C57H98O24 |
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Description
Brasilinolide A is a lactone produced by Nocardia brasiliensis.
Specification
| Synonyms | Propanedioic acid, mono(14-(6-((2,6-dideoxy-3-O-(1-oxopentyl)-beta-D-lyxo-hexopyranosyl)oxy)-2,4-dihydroxy-1,3,5-trimethylheptyl)-3,9,20,22,24,28,30,31,32-nonahydroxy-13,27-dimethyl-16-oxo-11,15,34-trioxatricyclo(28.3.1.0(sup 10,12))tetratriacont-17-en-5-yl) ester; 3-[[2,4-dihydroxy-6-(5-hydroxy-6-methyl-4-pentanoyloxy-tetrahydropyran-2-yl)oxy-1,3,5-trimethyl-heptyl]-nonahydroxy-dimethyl-oxo-[?]yl]oxy-3-oxo-propanoic acid |
| IUPAC Name | 3-[[(1R,17E,30R,31R,32S)-14-[3,5-dihydroxy-7-(5-hydroxy-6-methyl-4-pentanoyloxyoxan-2-yl)oxy-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]oxy]-3-oxopropanoic acid |
| Canonical SMILES | CCCCC(=O)OC1CC(OC(C1O)C)OC(C)C(C)C(C(C)C(C(C)C2C(C3C(O3)C(CCCC(CC(CC4CC(C(C(O4)(CC(C(CCC(CC(CC(CC=CC(=O)O2)O)O)O)C)O)O)O)O)O)OC(=O)CC(=O)O)O)C)O)O |
| InChI | InChI=1S/C57H98O24/c1-9-10-16-46(67)78-44-25-49(76-34(8)52(44)72)75-33(7)29(3)50(70)30(4)51(71)31(5)53-32(6)54-55(80-54)41(62)15-12-14-39(77-48(69)26-45(65)66)22-38(61)23-40-24-42(63)56(73)57(74,81-40)27-43(64)28(2)18-19-36(59)21-37(60)20-35(58)13-11-17-47(68)79-53/h11,17,28-44,49-56,58-64,70-74H,9-10,12-16,18-27H2,1-8H3,(H,65,66)/b17-11+/t28?,29?,30?,31?,32?,33?,34?,35?,36?,37?,38?,39?,40-,41?,42+,43?,44?,49?,50?,51?,52?,53?,54?,55?,56-,57-/m1/s1 |
| InChI Key | MVSIZSYJQDRVAV-FSWGJMNFSA-N |
Properties
| Appearance | Powder |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 1230.3°C at 760 mmHg |
| Density | 1.33 g/cm3 |
| Solubility | Soluble in Water, methanol, ethanol, DMSO |
Reference Reading
1. 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.
2. Absolute stereochemistry of immunosuppressive macrolide brasilinolide A and its new congener brasilinolide C
Kazusei Komatsu, Masashi Tsuda, Yasushi Tanaka, Yuzuru Mikami, Jun'ichi Kobayashi J Org Chem. 2004 Mar 5;69(5):1535-41. doi: 10.1021/jo035773v.
Brasilinolide A (2) is a 32-membered polyhydroxyl macrolide with immunosuppressive activity isolated from a pathogenic actinomycete, Nocardia brasiliensis IFM0406. The absolute configurations at 26 chiral centers of 2 and its new congener, brasilinolide C (1), were determined on the basis of the spectral data of 1 and degradation products derived from 1 and 2.
3. 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.
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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 ╳
