Fusicoccin | CAS#20108-30-9 | CaMKK2/14-3-3 natural stabilizer

MedKoo Cat#: 463439 | Name: Fusicoccin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Fusicoccin is a natural Stabilizer of Protein-Protein Interactions between CaMKK2 and 14-3-3.

Chemical Structure

Fusicoccin

CAS#20108-30-9

Theoretical Analysis

MedKoo Cat#: 463439

Name: Fusicoccin

CAS#: 20108-30-9

Chemical Formula: C36H56O12

Exact Mass: 680.3772

Molecular Weight: 680.83

Elemental Analysis: C, 63.51; H, 8.29; O, 28.20

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

No Data

Synonym

Fusicoccin;

IUPAC/Chemical Name

(S)-2-((1S,4R,5R,6R,6aS,9S,10aR,E)-4-(((2S,3R,4S,5R,6R)-4-acetoxy-3,5-dihydroxy-6-(((2-methylbut-3-en-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-1,5-dihydroxy-9-(methoxymethyl)-6,10a-dimethyl-1,2,4,5,6,6a,7,8,9,10a-decahydrodicyclopenta[a,d][8]annulen-3-yl)propyl acetate

InChi Key

KXTYBXCEQOANSX-WYKQKOHHSA-N

InChi Code

InChI=1S/C36H56O12/c1-10-35(6,7)45-17-26-30(41)33(46-21(5)38)31(42)34(47-26)48-32-28-24(18(2)15-44-20(4)37)13-27(39)36(28,8)14-25-22(16-43-9)11-12-23(25)19(3)29(32)40/h10,14,18-19,22-23,26-27,29-34,39-42H,1,11-13,15-17H2,2-9H3/b25-14-/t18-,19-,22-,23+,26-,27+,29-,30-,31-,32-,33+,34-,36+/m1/s1

SMILES Code

CC(OC[C@H](C1=C2[C@@H](O[C@H]3O[C@H](COC(C=C)(C)C)[C@@H](O)[C@H](OC(C)=O)[C@H]3O)[C@H](O)[C@H](C)[C@]4([H])CC[C@H](COC)/C4=C/[C@@]2(C)[C@@H](O)C1)C)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 680.83 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Lentini Santo D, Petrvalska O, Obsilova V, Ottmann C, Obsil T. Stabilization of Protein-Protein Interactions between CaMKK2 and 14-3-3 by Fusicoccins. ACS Chem Biol. 2020 Nov 4. doi: 10.1021/acschembio.0c00821. Epub ahead of print. PMID: 33146997. 2: Sengupta A, Liriano J, Bienkiewicz EA, Miller BG, Frederich JH. Probing the 14-3-3 Isoform-Specificity Profile of Protein-Protein Interactions Stabilized by Fusicoccin A. ACS Omega. 2020 Sep 24;5(39):25029-25035. doi: 10.1021/acsomega.0c01454. PMID: 33043180; PMCID: PMC7542595. 3: Roblin G, Bonnemain JL, Chollet JF. Auxinic herbicide conjugates with an α-amino acid function: Structural requirements for biological activity on motor cells. Plant Physiol Biochem. 2020 Oct;155:444-454. doi: 10.1016/j.plaphy.2020.07.014. Epub 2020 Aug 2. PMID: 32818792. 4: Li C, Huang D, Wang C, Wang N, Yao Y, Li W, Liao W. NO is involved in H2-induced adventitious rooting in cucumber by regulating the expression and interaction of plasma membrane H+-ATPase and 14-3-3. Planta. 2020 Jun 29;252(1):9. doi: 10.1007/s00425-020-03416-z. PMID: 32602044. 5: Harmange Magnani CS, Maimone TJ. Fusicoccin Keeps Getting Stickier: Modulation of an Adaptor Protein Interactome with a Molecular Glue Leads to Neurite Outgrowth. Cell Chem Biol. 2020 Jun 18;27(6):635-637. doi: 10.1016/j.chembiol.2020.05.011. PMID: 32559498. 6: Demes E, Besse L, Cubero-Font P, Satiat-Jeunemaitre B, Thomine S, De Angeli A. Dynamic measurement of cytosolic pH and [NO3-] uncovers the role of the vacuolar transporter AtCLCa in cytosolic pH homeostasis. Proc Natl Acad Sci U S A. 2020 Jun 30;117(26):15343-15353. doi: 10.1073/pnas.2007580117. Epub 2020 Jun 16. PMID: 32546525; PMCID: PMC7334523. 7: Kutschera U, Khanna R. Auxin action in developing maize coleoptiles: challenges and open questions. Plant Signal Behav. 2020 Jun 2;15(6):1762327. doi: 10.1080/15592324.2020.1762327. Epub 2020 May 13. PMID: 32403974. 8: Gannon M, Yacoubian TA. 007 (x2)-3-3: 14-3-3 Targeted Compounds as Double Agents. Trends Pharmacol Sci. 2020 Jul;41(7):431-433. doi: 10.1016/j.tips.2020.05.001. Epub 2020 May 10. PMID: 32402470; PMCID: PMC7478911. 9: Weng L, Zhang M, Wang K, Chen G, Ding M, Yuan W, Zhu Y, Xu W, Xu F. Potassium alleviates ammonium toxicity in rice by reducing its uptake through activation of plasma membrane H+-ATPase to enhance proton extrusion. Plant Physiol Biochem. 2020 Jun;151:429-437. doi: 10.1016/j.plaphy.2020.03.040. Epub 2020 Apr 2. Erratum in: Plant Physiol Biochem. 2020 Oct;155:987. PMID: 32289636. 10: Bosica F, Andrei SA, Neves JF, Brandt P, Gunnarsson A, Landrieu I, Ottmann C, O'Mahony G. Design of Drug-Like Protein-Protein Interaction Stabilizers Guided By Chelation-Controlled Bioactive Conformation Stabilization. Chemistry. 2020 Jun 2;26(31):7131-7139. doi: 10.1002/chem.202001608. Epub 2020 May 11. PMID: 32255539. 11: Kaplan A, Andrei SA, van Regteren Altena A, Simas T, Banerjee SL, Kato N, Bisson N, Higuchi Y, Ottmann C, Fournier AE. Polypharmacological Perturbation of the 14-3-3 Adaptor Protein Interactome Stimulates Neurite Outgrowth. Cell Chem Biol. 2020 Jun 18;27(6):657-667.e6. doi: 10.1016/j.chembiol.2020.02.010. Epub 2020 Mar 26. PMID: 32220335. 12: Ye W, Ando E, Rhaman MS, Tahjib-Ul-Arif M, Okuma E, Nakamura Y, Kinoshita T, Murata Y. Inhibition of light-induced stomatal opening by allyl isothiocyanate does not require guard cell cytosolic Ca2+ signaling. J Exp Bot. 2020 May 30;71(10):2922-2932. doi: 10.1093/jxb/eraa073. PMID: 32103265; PMCID: PMC7260714. 13: Kuusk A, Boyd H, Chen H, Ottmann C. Small-molecule modulation of p53 protein-protein interactions. Biol Chem. 2020 Jul 28;401(8):921-931. doi: 10.1515/hsz-2019-0405. PMID: 32049643. 14: Masuda R, Kawasaki Y, Igawa K, Manabe Y, Fujii H, Kato N, Tomooka K, Ohkanda J. Copper-Free Huisgen Cycloaddition for the 14-3-3-Templated Synthesis of Fusicoccin-Peptide Conjugates. Chem Asian J. 2020 Mar 16;15(6):742-747. doi: 10.1002/asia.202000042. Epub 2020 Feb 18. PMID: 32017414. 15: Xin X, Lei L, Zheng Y, Zhang T, Pingali SV, O'Neill H, Cosgrove DJ, Li S, Gu Y. Cellulose synthase interactive1- and microtubule-dependent cell wall architecture is required for acid growth in Arabidopsis hypocotyls. J Exp Bot. 2020 May 30;71(10):2982-2994. doi: 10.1093/jxb/eraa063. PMID: 32016356; PMCID: PMC7260726. 16: Sengupta A, Liriano J, Miller BG, Frederich JH. Analysis of Interactions Stabilized by Fusicoccin A Reveals an Expanded Suite of Potential 14-3-3 Binding Partners. ACS Chem Biol. 2020 Feb 21;15(2):305-310. doi: 10.1021/acschembio.9b00795. Epub 2020 Jan 29. PMID: 31971771; PMCID: PMC7169973. 17: Bjørk PK, Rasmussen SA, Gjetting SK, Havshøi NW, Petersen TI, Ipsen JØ, Larsen TO, Fuglsang AT. Tenuazonic acid from Stemphylium loti inhibits the plant plasma membrane H+ -ATPase by a mechanism involving the C-terminal regulatory domain. New Phytol. 2020 May;226(3):770-784. doi: 10.1111/nph.16398. Epub 2020 Feb 3. PMID: 31880817; PMCID: PMC7187312. 18: Gigante A, Sijbesma E, Sánchez-Murcia PA, Hu X, Bier D, Bäcker S, Knauer S, Gago F, Ottmann C, Schmuck C. A Supramolecular Stabilizer of the 14-3-3ζ/ERα Protein-Protein Interaction with a Synergistic Mode of Action. Angew Chem Int Ed Engl. 2020 Mar 23;59(13):5284-5287. doi: 10.1002/anie.201914517. Epub 2020 Feb 11. PMID: 31814236; PMCID: PMC7155037. 19: Kumari A, Chételat A, Nguyen CT, Farmer EE. Arabidopsis H+-ATPase AHA1 controls slow wave potential duration and wound- response jasmonate pathway activation. Proc Natl Acad Sci U S A. 2019 Oct 1;116(40):20226-20231. doi: 10.1073/pnas.1907379116. Epub 2019 Sep 16. PMID: 31527254; PMCID: PMC6778210. 20: Adamowski M, Li L, Friml J. Reorientation of Cortical Microtubule Arrays in the Hypocotyl of Arabidopsis thaliana Is Induced by the Cell Growth Process and Independent of Auxin Signaling. Int J Mol Sci. 2019 Jul 7;20(13):3337. doi: 10.3390/ijms20133337. PMID: 31284661; PMCID: PMC6651120.