FK1012

FK1012 is a dimer consisting of two molecules of FK506 (tacrolimus) linked via their vinyl groups.[1] It is used as a research tool in chemically induced dimerization applications. FK506 binding proteins (FKBPs) do not normally form dimers but can be caused to dimerize in the presence of FK1012. Genetically engineered proteins based on FKBPs can be used to manipulate protein localization, signalling pathways and protein activation.[2]

FK1012
Names
IUPAC name
(1R,12S,13R,14S,18E,21S,23S,24R,25R,27R)-1,14-Dihydroxy-17-{(2E)-4-[(12S,13R,14S,17R,18E,21S,23S,24R,25R,27R)-14-hydroxy-12-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-propen-2-yl}-23,25-dimethoxy-13,19,21,27-tetramethyl-2,3,10,16-tetraoxo-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-en-17-yl]-2-buten-1-yl}-12-{(1E)-1-[(1R,3R,4R)-4-hydroxy-3-methoxycyclohexyl]-1-propen-2-yl}-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9]octacos-18-ene-2,3,10,16-tetrone
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
  • InChI=1S/C86H134N2O23/c1-47-33-49(3)37-71(104-13)79-73(106-15)41-53(7)78(108-79)75(95)82(97)87-31-21-19-25-61(87)84(99)109-76(51(5)39-57-27-29-63(89)69(43-57)102-11)55(9)65(91)45-67(93)59(35-47)23-17-18-24-60-36-48(2)34-50(4)38-72(105-14)80-74(107-16)42-54(8)86(101,111-80)81(96)83(98)88-32-22-20-26-62(88)85(100)110-77(56(10)66(92)46-68(60)94)52(6)40-58-28-30-64(90)70(44-58)103-12/h17-18,35-36,39-40,49-50,53-66,69-74,76-80,89-92,101H,19-34,37-38,41-46H2,1-16H3/b18-17+,47-35+,48-36+,51-39+,52-40+/t49-,50-,53+,54+,55+,56+,57-,58-,59+,60?,61?,62?,63+,64+,65-,66-,69+,70+,71-,72-,73+,74+,76+,77+,78?,79+,80+,86+/m0/s1
    Key: IOISFHIZCFPBTB-HSZXOJBTSA-N
  • C[C@@H]1C[C@@H]([C@@H]2[C@@H](C[C@H](C(O2)C(=O)C(=O)N3CCCCC3C(=O)O[C@@H]([C@@H]([C@H](CC(=O)[C@@H](/C=C(/C1)\C)C/C=C/CC4/C=C(/C[C@@H](C[C@@H]([C@@H]5[C@@H](C[C@H]([C@@](O5)(C(=O)C(=O)N6CCCCC6C(=O)O[C@@H]([C@@H]([C@H](CC4=O)O)C)/C(=C/[C@@H]7CC[C@H]([C@@H](C7)OC)O)/C)O)C)OC)OC)C)\C)O)C)/C(=C/[C@@H]8CC[C@H]([C@@H](C8)OC)O)/C)C)OC)OC
Properties
C86H134N2O23
Molar mass 1564.009 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Steven T. Diver; Stuart L. Schreiber (1997). "Single-step syntheses of cell permeable protein dimerizers that activate signal transduction and gene expression". J. Am. Chem. Soc. 119 (22): 5106–5109. doi:10.1021/ja963891c.
  2. Fegan, A; White, B; Carlson, JC; Wagner, CR (Jun 9, 2010). "Chemically controlled protein assembly: techniques and applications". Chemical Reviews. 110 (6): 3315–36. doi:10.1021/cr8002888. PMID 20353181.

Further reading


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