Synonym
SB-217452; SB 217452; SB217452;
IUPAC/Chemical Name
(2R,3S)-2-((S)-2-amino-3-hydroxypropanamido)-3-((2R,3R,4R,5R)-5-((E)-4-(carbamoylimino)-3-methyl-2-oxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrothiophen-2-yl)-3-hydroxypropanoic acid
InChi Key
NGJDTPRGDCKRHD-DWRMSLKJSA-N
InChi Code
InChI=1S/C16H24N6O9S/c1-21-6(19-15(18)30)2-3-22(16(21)31)13-10(26)9(25)11(32-13)8(24)7(14(28)29)20-12(27)5(17)4-23/h2-3,5,7-11,13,23-26H,4,17H2,1H3,(H2,18,30)(H,20,27)(H,28,29)/b19-6+/t5-,7+,8-,9+,10+,11+,13+/m0/s1
SMILES Code
CN(C1=O)/C(C=CN1[C@H]2[C@@H]([C@H]([C@H](S2)[C@H]([C@H](C(O)=O)NC([C@H](CO)N)=O)O)O)O)=N/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
476.46
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: Ushimaru R, Chen Z, Zhao H, Fan PH, Liu HW. Identification of the Enzymes Mediating the Maturation of the Seryl-tRNA Synthetase Inhibitor SB-217452 during the Biosynthesis of Albomycins. Angew Chem Int Ed Engl. 2020 Feb 24;59(9):3558-3562. doi: 10.1002/anie.201915275. Epub 2020 Jan 29. PMID: 31863717; PMCID: PMC7138408.
2: Saha A, Dutta S, Nandi N. Inhibition of seryl tRNA synthetase by seryl nucleoside moiety (SB-217452) of albomycin antibiotic. J Biomol Struct Dyn. 2020 May;38(8):2440-2454. doi: 10.1080/07391102.2019.1635912. Epub 2019 Jul 1. PMID: 31241419.
3: Kim JY, Carlson BA, Xu XM, Zeng Y, Chen S, Gladyshev VN, Lee BJ, Hatfield DL. Inhibition of selenocysteine tRNA[Ser]Sec aminoacylation provides evidence that aminoacylation is required for regulatory methylation of this tRNA. Biochem Biophys Res Commun. 2011 Jun 17;409(4):814-9. doi: 10.1016/j.bbrc.2011.05.096. Epub 2011 May 23. PMID: 21624347; PMCID: PMC3124823.
4: Zeng Y, Roy H, Patil PB, Ibba M, Chen S. Characterization of two seryl-tRNA synthetases in albomycin-producing Streptomyces sp. strain ATCC 700974. Antimicrob Agents Chemother. 2009 Nov;53(11):4619-27. doi: 10.1128/AAC.00782-09. Epub 2009 Aug 31. PMID: 19721072; PMCID: PMC2772349.
5: Stefanska AL, Fulston M, Houge-Frydrych CS, Jones JJ, Warr SR. A potent seryl tRNA synthetase inhibitor SB-217452 isolated from a Streptomyces species. J Antibiot (Tokyo). 2000 Dec;53(12):1346-53. doi: 10.7164/antibiotics.53.1346. PMID: 11217799.
