Synonym
RK682; RK 682; RK-682
IUPAC/Chemical Name
(R)-3-Hexadecanoyl-5-hydroxymethyltetronic acid
InChi Key
CPQQKPHTOQWKMF-MRTLOADZSA-N
InChi Code
InChI=1S/C21H36O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17(23)19-20(24)18(16-22)26-21(19)25/h18-19,22H,2-16H2,1H3/t18-,19?/m1/s1
SMILES Code
O=C(C1C(CCCCCCCCCCCCCCC)=O)O[C@H](CO)C1=O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
368.51
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 |
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4: Sun Y, Hahn F, Demydchuk Y, Chettle J, Tosin M, Osada H, Leadlay PF. In vitro reconstruction of tetronate RK-682 biosynthesis. Nat Chem Biol. 2010 Feb;6(2):99-101. doi: 10.1038/nchembio.285. Epub 2009 Dec 20. PubMed PMID: 20081823; PubMed Central PMCID: PMC2811812.
5: Schobert R, Jagusch C. Solution-phase and solid-phase syntheses of enzyme inhibitor RK-682 and antibiotic agglomerins. J Org Chem. 2005 Jul 22;70(15):6129-32. PubMed PMID: 16018718.
6: Usui T, Kojima S, Kidokoro S, Ueda K, Osada H, Sodeoka M. Design and synthesis of a dimeric derivative of RK-682 with increased inhibitory activity against VHR, a dual-specificity ERK phosphatase: implications for the molecular mechanism of the inhibition. Chem Biol. 2001 Dec;8(12):1209-20. PubMed PMID: 11755399.
7: Sodeoka M, Sampe R, Kojima S, Baba Y, Morisaki N, Hashimoto Y. Asymmetric synthesis of a 3-acyltetronic acid derivative, RK-682, and formation of its calcium salt during silica gel column chromatography. Chem Pharm Bull (Tokyo). 2001 Feb;49(2):206-12. PubMed PMID: 11217111.
8: Hamaguchi T, Sudo T, Osada H. RK-682, a potent inhibitor of tyrosine phosphatase, arrested the mammalian cell cycle progression at G1phase. FEBS Lett. 1995 Sep 18;372(1):54-8. PubMed PMID: 7556642.
