L-659,699
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 532062

CAS#: 29066-42-0

Description: L-659,699, also known as hymeglusin, is a fungal β-lactone antibiotic that inhibits HMG-CoA synthase (IC50 = 0.12 μM) by covalently modifying the active Cys129 residue of the enzyme.


Price and Availability

Size
Price

1mg
USD 360
Size
Price

3mg
USD 700
Size
Price

L-659,699, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 532062
Name: L-659,699
CAS#: 29066-42-0
Chemical Formula: C18H28O5
Exact Mass: 324.1937
Molecular Weight: 324.42
Elemental Analysis: C, 66.64; H, 8.70; O, 24.66


Synonym: Hymeglusin; L-659,699; L 659,699; L659,699.

IUPAC/Chemical Name: (2E,4E,7R)-11-[(2R,3R)-3-(hydroxymethyl)-4-oxooxetan-2-yl]-3,5,7-trimethylundeca-2,4-dienoic acid

InChi Key: ODCZJZWSXPVLAW-KXCGKLMDSA-N

InChi Code: InChI=1S/C18H28O5/c1-12(8-13(2)9-14(3)10-17(20)21)6-4-5-7-16-15(11-19)18(22)23-16/h9-10,12,15-16,19H,4-8,11H2,1-3H3,(H,20,21)/b13-9+,14-10+/t12-,15-,16-/m1/s1

SMILES Code: O=C(O)/C=C(C)/C=C(C)/C[C@H](C)CCCC[C@H]([C@H]1CO)OC1=O


Technical Data

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:
>2 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).

Harmonized System Code:
293490


References

1: Skaff DA, Ramyar KX, McWhorter WJ, Barta ML, Geisbrecht BV, Miziorko HM. Biochemical and structural basis for inhibition of Enterococcus faecalis hydroxymethylglutaryl-CoA synthase, mvaS, by hymeglusin. Biochemistry. 2012 Jun 12;51(23):4713-22. doi: 10.1021/bi300037k. PubMed PMID: 22510038; PubMed Central PMCID: PMC3431454.

2: Carazo A, Alejandre MJ, Louktibi A, Linares A. The reversal of the inhibition on lipids synthesis by L-659,699 in arterial smooth muscle cells cultures. Mol Cell Biochem. 2001 May;221(1-2):25-31. PubMed PMID: 11506182.

3: Ginger ML, Chance ML, Sadler IH, Goad LJ. The biosynthetic incorporation of the intact leucine skeleton into sterol by the trypanosomatid Leishmania mexicana. J Biol Chem. 2001 Apr 13;276(15):11674-82. PubMed PMID: 11148203.

4: Rokosz LL, Boulton DA, Butkiewicz EA, Sanyal G, Cueto MA, Lachance PA, Hermes JD. Human cytoplasmic 3-hydroxy-3-methylglutaryl coenzyme A synthase: expression, purification, and characterization of recombinant wild-type and Cys129 mutant enzymes. Arch Biochem Biophys. 1994 Jul;312(1):1-13. PubMed PMID: 7913309.

5: Giron MD, Havel CM, Watson JA. Isopentenoid synthesis in eukaryotic cells. An initiating role for post-translational control of 3-hydroxy-3-methylglutaryl coenzyme A reductase. Arch Biochem Biophys. 1993 Apr;302(1):265-71. PubMed PMID: 8097083.

6: Greenspan MD, Bull HG, Yudkovitz JB, Hanf DP, Alberts AW. Inhibition of 3-hydroxy-3-methylglutaryl-CoA synthase and cholesterol biosynthesis by beta-lactone inhibitors and binding of these inhibitors to the enzyme. Biochem J. 1993 Feb 1;289 ( Pt 3):889-95. PubMed PMID: 8094614; PubMed Central PMCID: PMC1132259.

7: Greenspan MD, Yudkovitz JB, Lo CY, Chen JS, Alberts AW, Hunt VM, Chang MN, Yang SS, Thompson KL, Chiang YC, et al. Inhibition of hydroxymethylglutaryl-coenzyme A synthase by L-659,699. Proc Natl Acad Sci U S A. 1987 Nov;84(21):7488-92. PubMed PMID: 2890166; PubMed Central PMCID: PMC299321.