Tetrafibricin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-03109 |
| CAS | 151705-56-5 |
| Molecular Weight | 781.97 |
| Molecular Formula | C41H67NO13 |
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Description
Tetrafibricin is a fibrinogen antagonist produced by Str. neyagawaensis NR0577. Tetrafibricin has a strong inhibitory effect on the binding of fibrinogen to the GP IIb/IIIa receptor with an IC50 of 46 nmol/L, and an IC50 of 46 mol/L for the inhibition of HeLa cell toxicity.
Specification
| Synonyms | 11,15,17,19,23,25,27,29,33,37-Decahydroxy-12-methyl-13-oxo-40-amino-2,4,6,8,20,30,34-tetracontaheptaenoic acid; 2,4,6,8,20,30,34-Tetracontaheptaenoic acid, 40-amino-11,15,17,19,23,25,27,29,33,37-decahydroxy-12-methyl-13-oxo- |
| IUPAC Name | (2E,4E,6E,8E,20E,30E,34E)-40-amino-11,15,17,19,23,25,27,29,33,37-decahydroxy-12-methyl-13-oxotetraconta-2,4,6,8,20,30,34-heptaenoic acid |
| Canonical SMILES | CC(C(CC=CC=CC=CC=CC(=O)O)O)C(=O)CC(CC(CC(C=CCC(CC(CC(CC(C=CCC(C=CCC(CCCN)O)O)O)O)O)O)O)O)O |
| InChI | InChI=1S/C41H67NO13/c1-29(39(52)20-7-5-3-2-4-6-8-21-41(54)55)40(53)28-38(51)27-37(50)25-34(47)18-11-17-33(46)24-36(49)26-35(48)23-32(45)16-10-15-30(43)13-9-14-31(44)19-12-22-42/h2-11,13,16,18,21,29-39,43-52H,12,14-15,17,19-20,22-28,42H2,1H3,(H,54,55)/b3-2+,6-4+,7-5+,13-9+,16-10+,18-11+,21-8+ |
| InChI Key | BIOWDMWPQOMXJO-YHYSRAEPSA-N |
Properties
| Appearance | Light Yellow Powder |
| Boiling Point | 1024.7±65.0°C at 760 mmHg |
Reference Reading
1. Inspirations from tetrafibricin and related polyketides: new methods and strategies for 1,5-polyol synthesis
Ryan M Friedrich, Gregory K Friestad Nat Prod Rep. 2020 Sep 23;37(9):1229-1261. doi: 10.1039/c9np00070d.
Covering: up to 2019 Selective synthesis with control of remote stereogenic centers has long been a challenge in organic chemistry. In recent years the interest in this topic has been energized by isolation and synthetic studies of tetrafibricin and other natural products containing 1,5-polyols, such as amphidinol 3, marinomycins, and caylobolide. Here we discuss recent developments in 1,5-polyol synthesis, including an overview of selected bioactive natural products in this class and examples of new synthetic methodologies and strategies dedicated to remote stereocontrol in these structures. To illustrate in greater depth, we review several instructive examples of how these innovations have been applied in synthetic studies on tetrafibricin.
2. Development of a Double Allylboration Reagent Targeting 1,5-syn-(E)-Diols: Application to the Synthesis of the C(23)-C(40) Fragment of Tetrafibricin
Philippe Nuhant, Jeremy Kister, Ricardo Lira, Achim Sorg, William R Roush Tetrahedron. 2011 Sep 2;67(35):6497-6512. doi: 10.1016/j.tet.2011.06.008.
Interest in the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin prompted us to develop a new method for the synthesis of 1,5-syn-(E)-diols. Toward this end, the kinetically controlled hydroboration of allenes 6, 33, ent-39, 42 and 45 with the Soderquist borane 25R were studied. Tetrabutylammonium allenyltrifluoroborate 45 gave superior results and was utilized in a double allylboration sequence with two different aldehydes to provide the targeted 1,5-syn-(E)-diols in generally high yields (72-98%), and with high enantioselectivity (>95% e.e.), diastereoselectivity (d.r. >20:1), and (E)/(Z) selectivity (>20:1). This new method was applied to the synthesis of the C(23)-C(40) fragment 2 of tetrafibricin.
3. Asymmetric alcohol C-H allylation and syn-crotylation: C9-C20 of tetrafibricin
Takahiko Itoh, T Patrick Montgomery, Antonio Recio rd, Michael J Krische Org Lett. 2014 Feb 7;16(3):820-3. doi: 10.1021/ol403566w. Epub 2014 Jan 14.
The C9-C20 segment of the fibrinogen receptor inhibitor tetrafibricin was prepared in 10 steps (longest linear sequence). Ruthenium catalyzed enantioselective syn-crotylation is used to construct C9-C13. Iridium catalyzed asymmetric alcohol C-H allylation of a commercial malic acid derived alcohol is used to construct C14-C20. Recovery and recycling of the iridium catalyst is described.
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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 ╳
