Synonym
Tryptophyl adenylate;
IUPAC/Chemical Name
(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-((phosphonooxy)methyl)tetrahydrofuran-3-yl L-tryptophanate
InChi Key
ZTKQHOGBACRMGC-SQIXAUHQSA-N
InChi Code
1S/C21H24N7O8P/c22-12(5-10-6-24-13-4-2-1-3-11(10)13)21(30)36-17-14(7-34-37(31,32)33)35-20(16(17)29)28-9-27-15-18(23)25-8-26-19(15)28/h1-4,6,8-9,12,14,16-17,20,24,29H,5,7,22H2,(H2,23,25,26)(H2,31,32,33)/t12-,14+,16+,17+,20+/m0/s1
SMILES Code
O=C(O[C@@H]1[C@@H](COP(O)(O)=O)O[C@@H](n2c3ncnc(N)c3nc2)[C@@H]1O)[C@@H](N)Cc4c[nH]c5c4cccc5
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
533.43
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: Merle M, Trezeguet V, Graves PV, Andrews D, Muench KH, Labouesse B. Tryptophanyl adenylate formation by tryptophanyl-tRNA synthetase from Escherichia coli. Biochemistry. 1986 Mar 11;25(5):1115-23. PubMed PMID: 3516215.
2: Mazat JP, Merle M, Graves PV, Merault G, Gandar JC, Labouesse B. Kinetic anticooperativity in pre-steady-state formation of tryptophanyl adenylate by tryptophanyl-tRNA synthetase from beef pancreas. A consequence of the tryptophan anticooperative binding. Eur J Biochem. 1982 Nov 15;128(2-3):389-98. PubMed PMID: 7151786.
3: Koh CY, Kim JE, Napoli AJ, Verlinde CL, Fan E, Buckner FS, Van Voorhis WC, Hol WG. Crystal structures of Plasmodium falciparum cytosolic tryptophanyl-tRNA synthetase and its potential as a target for structure-guided drug design. Mol Biochem Parasitol. 2013 May;189(1-2):26-32. doi: 10.1016/j.molbiopara.2013.04.007. Epub 2013 May 7. PubMed PMID: 23665145; PubMed Central PMCID: PMC3680109.
4: Merault G, Labouesse J, Graves PV, Labouesse B. Kinetics of formation of tryptophanyl-adenylate by tryptophanyl-tRNA synthetase from beef pancreas. FEBS Lett. 1981 Jan 26;123(2):165-8. PubMed PMID: 6112162.
5: Favorova OO, Madoyan IA, Drutsa VL. "Half-site" affinity modification of tryptophanyl-tRNA synthetase leads to "freezing" of the free subunit. FEBS Lett. 1981 Jan 26;123(2):161-4. PubMed PMID: 6262106.
