Synonym
A 53868A; A-53868A; A53868A; Dehydrophos
IUPAC/Chemical Name
L-Leucinamide, glycyl-N-(2-phosphono-2-propenyl)-
InChi Key
CUTXECQUPHPKMN-VIFPVBQESA-N
InChi Code
InChI=1S/C11H22N3O5P/c1-7(2)4-9(11(13)16)14(10(15)5-12)6-8(3)20(17,18)19/h7,9H,3-6,12H2,1-2H3,(H2,13,16)(H2,17,18,19)/t9-/m0/s1
SMILES Code
CC(C)C[C@@H](C(N)=O)N(C(CN)=O)CC(P(O)(O)=O)=C
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).
HS Tariff Code
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
307.29
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: Bougioukou DJ, Mukherjee S, van der Donk WA. Revisiting the biosynthesis of dehydrophos reveals a tRNA-dependent pathway. Proc Natl Acad Sci U S A. 2013 Jul
2;110(27):10952-7. doi: 10.1073/pnas.1303568110. Epub 2013 Jun 17. PubMed PMID: 23776232; PubMed Central PMCID: PMC3704017.
2: Shao Z, Blodgett JA, Circello BT, Eliot AC, Woodyer R, Li G, van der Donk WA, Metcalf WW, Zhao H. Biosynthesis of 2-hydroxyethylphosphonate, an unexpected intermediate common to multiple phosphonate biosynthetic pathways. J Biol Chem. 2008 Aug 22;283(34):23161-8. doi: 10.1074/jbc.M801788200. Epub 2008 Jun 10.PubMed PMID: 18544530; PubMed Central PMCID: PMC2516978.
3: Hunt AH, Elzey TK. Revised structure of A53868A. J Antibiot (Tokyo). 1988 Jun;41(6):802. PubMed PMID: 3403375.
4: Whitteck JT, Ni W, Griffin BM, Eliot AC, Thomas PM, Kelleher NL, Metcalf WW, van der Donk WA. Reassignment of the structure of the antibiotic A53868 reveals an unusual amino dehydrophosphonic acid. Angew Chem Int Ed Engl. 2007;46(47):9089-92. PubMed PMID: 17990255.
5: Lee JH, Bae B, Kuemin M, Circello BT, Metcalf WW, Nair SK, van der Donk WA. Characterization and structure of DhpI, a phosphonate O-methyltransferase involved in dehydrophos biosynthesis. Proc Natl Acad Sci U S A. 2010 Oct 12;107(41):17557-62. doi: 10.1073/pnas.1006848107. Epub 2010 Sep 27. PubMed PMID: 20876132; PubMed Central PMCID: PMC2955109.
