Synonym
Valyl adenylate; Valyl-adenylate; Valyladenylate;
IUPAC/Chemical Name
(S)-2-amino-3-methylbutanoic (((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphoric) anhydride
InChi Key
KAVINRUMCQFLGF-NIXGFCADSA-N
InChi Code
InChI=1S/C15H23N6O8P/c1-6(2)8(16)15(24)29-30(25,26)27-3-7-10(22)11(23)14(28-7)21-5-20-9-12(17)18-4-19-13(9)21/h4-8,10-11,14,22-23H,3,16H2,1-2H3,(H,25,26)(H2,17,18,19)/t7-,8+,10-,11-,14-/m1/s1
SMILES Code
O=[P@](O)(OC[C@@H]1[C@H]([C@H]([C@H](n(cn2)c3c2c(N)ncn3)O1)O)O)OC([C@H](C(C)C)N)=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
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
446.35
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: Jakubowski H. Yellow lupin (Lupinus luteus) aminoacyl-tRNA synthetases. Isolation and some properties of enzyme-bound valyl adenylate and seryl adenylate. Biochim Biophys Acta. 1978 Dec 21;521(2):584-96. PubMed PMID: 32907.
2: Hountondji C, Lazennec C, Beauvallet C, Dessen P, Pernollet JC, Plateau P, Blanquet S. Crucial role of conserved lysine 277 in the fidelity of tRNA aminoacylation by Escherichia coli valyl-tRNA synthetase. Biochemistry. 2002 Dec 17;41(50):14856-65. PubMed PMID: 12475234.
3: Silvian LF, Wang J, Steitz TA. Insights into editing from an ile-tRNA synthetase structure with tRNAile and mupirocin. Science. 1999 Aug 13;285(5430):1074-7. PubMed PMID: 10446055.
4: Southgate CC, Dixon HB. Phosphonate analogues of aminoacyl adenylates. Biochem J. 1978 Nov 1;175(2):461-5. PubMed PMID: 743207; PubMed Central PMCID: PMC1186092.
5: Dulic M, Perona JJ, Gruic-Sovulj I. Determinants for tRNA-dependent pretransfer editing in the synthetic site of isoleucyl-tRNA synthetase. Biochemistry. 2014 Oct 7;53(39):6189-98. doi: 10.1021/bi5007699. Epub 2014 Sep 23. PubMed PMID: 25207837; PubMed Central PMCID: PMC4188249.
6: Jakubowski H. The mechanism of inhibition of valyl-tRNA synthetase by S-adenosylhomocysteine. Biochim Biophys Acta. 1982 Dec 20;709(2):325-31. PubMed PMID: 7150609.
7: Fersht AR, Kaethner MM. Enzyme hyperspecificity. Rejection of threonine by the valyl-tRNA synthetase by misacylation and hydrolytic editing. Biochemistry. 1976 Jul 27;15(15):3342-6. PubMed PMID: 182209.
8: Nordin BE, Schimmel P. Transiently misacylated tRNA is a primer for editing of misactivated adenylates by class I aminoacyl-tRNA synthetases. Biochemistry. 2003 Nov 11;42(44):12989-97. PubMed PMID: 14596614.
9: Dulic M, Cvetesic N, Perona JJ, Gruic-Sovulj I. Partitioning of tRNA-dependent editing between pre- and post-transfer pathways in class I aminoacyl-tRNA synthetases. J Biol Chem. 2010 Jul 30;285(31):23799-809. doi: 10.1074/jbc.M110.133553. Epub 2010 May 24. PubMed PMID: 20498377; PubMed Central PMCID: PMC2911327.
10: Fukunaga R, Yokoyama S. Structural basis for substrate recognition by the editing domain of isoleucyl-tRNA synthetase. J Mol Biol. 2006 Jun 16;359(4):901-12. Epub 2006 Apr 25. PubMed PMID: 16697013.
11: Nomanbhoy TK, Schimmel PR. Misactivated amino acids translocate at similar rates across surface of a tRNA synthetase. Proc Natl Acad Sci U S A. 2000 May 9;97(10):5119-22. PubMed PMID: 10792042; PubMed Central PMCID: PMC25791.
12: Hendrickson TL, Nomanbhoy TK, de Crécy-Lagard V, Fukai S, Nureki O, Yokoyama S, Schimmel P. Mutational separation of two pathways for editing by a class I tRNA synthetase. Mol Cell. 2002 Feb;9(2):353-62. PubMed PMID: 11864608.
13: Borgford TJ, Gray TE, Brand NJ, Fersht AR. Site-directed mutagenesis reveals transition-state stabilization as a general catalytic mechanism for aminoacyl-tRNA synthetases. Biochemistry. 1987 Nov 17;26(23):7246-50. PubMed PMID: 3427072.
