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MedKoo Cat#: 597022 | Name: Thialysine HCl
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Thialysine, also known as S-Aminoethyl-l-cysteine or ACE, is a toxic analog of the amino acid lysine in which the second carbon of the amino acid's R-group (side chain) has been replaced with a sulfur atom. L-thialysine is known to have cytotoxic affects as it inhibits protein synthesis and lysine 2,3-aminomutase. Thialysine is utilized in protein synthesis and it is incorporated into proteins in place of lysine. is an alternative substrate useful for characterizing lysine cyclodeaminase from Streptomyces pristinaespiralis. AEC may be used as a non-antibiotic selection agent for genetically engineered soybeans expressing a lysine insensitive DHPS gene. AEC is being studied as an amino acid antibiotic.

Chemical Structure

Thialysine HCl
Thialysine HCl
CAS#4099-35-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 597022

Name: Thialysine HCl

CAS#: 4099-35-8 (HCl)

Chemical Formula: C5H13ClN2O2S

Exact Mass: 0.0000

Molecular Weight: 200.68

Elemental Analysis: C, 29.93; H, 6.53; Cl, 17.66; N, 13.96; O, 15.94; S, 15.98

Price and Availability

Size Price Availability Quantity
250mg USD 285.00 2 weeks
1g USD 450.00 2 weeks
5g USD 1,150.00 2 weeks
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Related CAS #
2936-69-8 (free base) 4099-35-8 (HCl)
Synonym
Thialysine hydrochloride; LJ 226; NSC 186915; NSC-186915; NSC186915;
IUPAC/Chemical Name
S-(2-aminoethyl)-L-cysteine hydrochloride
InChi Key
CVHKULVNPGAEQM-WCCKRBBISA-N
InChi Code
InChI=1S/C5H12N2O2S.ClH/c6-1-2-10-3-4(7)5(8)9;/h4H,1-3,6-7H2,(H,8,9);1H/t4-;/m0./s1
SMILES Code
N[C@@H](CSCCN)C(O)=O.[H]Cl
Appearance
Solid powder
Purity
>95% (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
More Info
Certificate of Analysis
CoA-Thialysine HCl-C23B10B19
Safety Data Sheet (SDS)
SDS-Thialysine HCl
Instruction
View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 200.68 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.

Recalculate based on batch purity %
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: Mattioli R, Pascarella G, D'Incà R, Cona A, Angelini R, Morea V, Tavladoraki P. Arabidopsis N-acetyltransferase activity 2 preferentially acetylates 1,3-diaminopropane and thialysine. Plant Physiol Biochem. 2022 Jan 1;170:123-132. doi: 10.1016/j.plaphy.2021.11.034. Epub 2021 Nov 24. PMID: 34871830. 2: Proietti G, Rainone G, Hintzen JCJ, Mecinović J. Exploring the Histone Acylome through Incorporation of γ-Thialysine on Histone Tails. Bioconjug Chem. 2020 Mar 18;31(3):844-851. doi: 10.1021/acs.bioconjchem.0c00012. Epub 2020 Feb 27. PMID: 32058696. 3: Al Temimi AHK, van der Wekken-de Bruijne R, Proietti G, Guo H, Qian P, Mecinović J. γ-Thialysine versus Lysine: An Insight into the Epigenetic Methylation of Histones. Bioconjug Chem. 2019 Jun 19;30(6):1798-1804. doi: 10.1021/acs.bioconjchem.9b00313. Epub 2019 Jun 5. PMID: 31117351. 4: Nagar M, Kumar H, Bearne SL. A platform for chemical modification of mandelate racemase: characterization of the C92S/C264S and γ-thialysine 166 variants. Protein Eng Des Sel. 2018 Apr 1;31(4):135-145. doi: 10.1093/protein/gzy011. PMID: 29850884. 5: Timms N, Windle CL, Polyakova A, Ault JR, Trinh CH, Pearson AR, Nelson A, Berry A. Structural insights into the recovery of aldolase activity in N-acetylneuraminic acid lyase by replacement of the catalytically active lysine with γ-thialysine by using a chemical mutagenesis strategy. Chembiochem. 2013 Mar 4;14(4):474-81. doi: 10.1002/cbic.201200714. Epub 2013 Feb 18. PMID: 23418011; PMCID: PMC3792637. 6: Hyvönen MT, Weisell J, Khomutov AR, Alhonen L, Vepsäläinen J, Keinänen TA. Metabolism of triethylenetetramine and 1,12-diamino-3,6,9-triazadodecane by the spermidine/spermine-N(1)-acetyltransferase and thialysine acetyltransferase. Drug Metab Dispos. 2013 Jan;41(1):30-2. doi: 10.1124/dmd.112.047274. Epub 2012 Sep 28. PMID: 23024204. 7: Maity AN, Shaikh AC, Srimurugan S, Wu CJ, Chen C, Ke SC. Synthesis of 4-thia-[6-(13)C]lysine from [2- (13)C]glycine: access to site-directed isotopomers of 2-aminoethanol, 2-bromoethylamine and 4-thialysine. Amino Acids. 2012 Jan;42(1):309-15. doi: 10.1007/s00726-010-0808-8. Epub 2010 Nov 20. PMID: 21103898. 8: Han BW, Bingman CA, Wesenberg GE, Phillips GN Jr. Crystal structure of Homo sapiens thialysine Nepsilon-acetyltransferase (HsSSAT2) in complex with acetyl coenzyme A. Proteins. 2006 Jul 1;64(1):288-93. doi: 10.1002/prot.20967. PMID: 16596569. 9: Lüersen K. Leishmania major thialysine Nepsilon-acetyltransferase: identification of amino acid residues crucial for substrate binding. FEBS Lett. 2005 Oct 10;579(24):5347-52. doi: 10.1016/j.febslet.2005.08.063. PMID: 16194533. 10: Abo-Dalo B, Ndjonka D, Pinnen F, Liebau E, Lüersen K. A novel member of the GCN5-related N-acetyltransferase superfamily from Caenorhabditis elegans preferentially catalyses the N-acetylation of thialysine [S-(2-aminoethyl)-L-cysteine]. Biochem J. 2004 Nov 15;384(Pt 1):129-37. doi: 10.1042/BJ20040789. PMID: 15283700; PMCID: PMC1134096. 11: Coleman CS, Stanley BA, Jones AD, Pegg AE. Spermidine/spermine-N1-acetyltransferase-2 (SSAT2) acetylates thialysine and is not involved in polyamine metabolism. Biochem J. 2004 Nov 15;384(Pt 1):139-48. doi: 10.1042/BJ20040790. PMID: 15283699; PMCID: PMC1134097. 12: Jun DY, Rue SW, Han KH, Taub D, Lee YS, Bae YS, Kim YH. Mechanism underlying cytotoxicity of thialysine, lysine analog, toward human acute leukemia Jurkat T cells. Biochem Pharmacol. 2003 Dec 15;66(12):2291-300. doi: 10.1016/j.bcp.2003.08.030. PMID: 14637187. 13: Miller J, Bandarian V, Reed GH, Frey PA. Inhibition of lysine 2,3-aminomutase by the alternative substrate 4-thialysine and characterization of the 4-thialysyl radical intermediate. Arch Biochem Biophys. 2001 Mar 15;387(2):281-8. doi: 10.1006/abbi.2001.2261. PMID: 11370852. 14: Gloss LM, Kirsch JF. Decreasing the basicity of the active site base, Lys-258, of Escherichia coli aspartate aminotransferase by replacement with gamma-thialysine. Biochemistry. 1995 Mar 28;34(12):3990-8. doi: 10.1021/bi00012a017. PMID: 7696264. 15: Sychrová H, Chevallier MR, Horák J, Kotyk A. Thialysine-resistant mutants and uptake of lysine in Schizosaccharomyces pombe. Curr Genet. 1992 Apr;21(4-5):351-5. doi: 10.1007/BF00351694. PMID: 1356078. 16: Ammon HL, Prasad SM, Gerlt JA. Structure of thialysine hydrochloride. Acta Crystallogr C. 1991 Jul 15;47 ( Pt 7):1476-8. doi: 10.1107/s0108270190012835. PMID: 1930822. 17: Di Girolamo M, Busiello V, Blarzino C, Cini C. Thialysine utilization for protein synthesis by an exponentially growing E. coli culture. Biochem Int. 1989 Dec;19(6):1195-203. PMID: 2561448. 18: Di Girolamo M, De Marco C, Blarzino C, Di Girolamo A, Foppoli C, Coccia R, Busiello V, Cini C. Isolation of thialysine--and selenalysine--resistant mutants of E. coli and CHO cells. Ital J Biochem. 1989 Jul-Aug;38(4):271A-273A. PMID: 2511161. 19: Di Girolamo M, Busiello V, Di Girolamo A, Foppoli C, De Marco C. Aspartokinase III repression in a thialysine-resistant mutant of E. coli. Biochem Int. 1988 Sep;17(3):545-54. PMID: 2849443. 20: Di Girolamo M, Coccia R, Blarzino C, Di Girolamo A, Busiello V. Degradation of thialysine- or selenalysine-containing abnormal proteins in E. coli. Biochem Int. 1988 Jun;16(6):1033-40. PMID: 3140818.