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

MedKoo CAT#: 597021

CAS#: 922-55-4

Description: Lanthionine is a thioether analogue of cystine; a component of lantibiotics (BACTERIOCINS).

Chemical Structure

CAS# 922-55-4

Theoretical Analysis

MedKoo Cat#: 597021
Name: Lanthionine
CAS#: 922-55-4
Chemical Formula: C6H12N2O4S
Exact Mass: 208.0518
Molecular Weight: 208.23
Elemental Analysis: C, 34.61; H, 5.81; N, 13.45; O, 30.73; S, 15.40

Price and Availability

Size Price Availability Quantity
100.0mg USD 450.0 2 Weeks
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Synonym: Lanthionine; L-Lanthionine; NSC 83248; NSC-83248; NSC83248;

IUPAC/Chemical Name: (2R,2'R)-3,3'-thiobis(2-aminopropanoic acid)


InChi Code: InChI=1S/C6H12N2O4S/c7-3(5(9)10)1-13-2-4(8)6(11)12/h3-4H,1-2,7-8H2,(H,9,10)(H,11,12)/t3-,4-/m0/s1

SMILES Code: N[C@@H](CSC[C@H](N)C(O)=O)C(O)=O

Appearance: Solid powder

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 208.23 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

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1: Dutta D, Lai KY, Reyes-Ordoñez A, Chen J, van der Donk WA. Lanthionine synthetase C-like protein 2 (LanCL2) is Important for Adipogenic Differentiation. J Lipid Res. 2018 Jun 7. pii: jlr.M085274. doi: 10.1194/jlr.M085274. [Epub ahead of print] PubMed PMID: 29880530.

2: Bobeica SC, van der Donk WA. The Enzymology of Prochlorosin Biosynthesis. Methods Enzymol. 2018;604:165-203. doi: 10.1016/bs.mie.2018.01.038. Epub 2018 Mar 12. PubMed PMID: 29779652.

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4: Ebner P, Reichert S, Luqman A, Krismer B, Popella P, Götz F. Lantibiotic production is a burden for the producing staphylococci. Sci Rep. 2018 May 10;8(1):7471. doi: 10.1038/s41598-018-25935-2. PubMed PMID: 29749386; PubMed Central PMCID: PMC5945643.

5: Dhar I, Svingen GFT, Pedersen ER, DeRatt B, Ulvik A, Strand E, Ueland PM, Bønaa KH, Gregory JF, Nygård OK. Plasma cystathionine and risk of acute myocardial infarction among patients with coronary heart disease: Results from two independent cohorts. Int J Cardiol. 2018 Sep 1;266:24-30. doi: 10.1016/j.ijcard.2018.04.083. Epub 2018 Apr 21. PubMed PMID: 29728335.

6: Leber A, Hontecillas R, Zoccoli-Rodriguez V, Bassaganya-Riera J. Activation of LANCL2 by BT-11 Ameliorates IBD by Supporting Regulatory T Cell Stability Through Immunometabolic Mechanisms. Inflamm Bowel Dis. 2018 Apr 28. doi: 10.1093/ibd/izy167. [Epub ahead of print] PubMed PMID: 29718324.

7: Denoel T, Lemaire C, Luxen A. Progress in lanthionine and protected lanthionine synthesis. Chemistry. 2018 May 1. doi: 10.1002/chem.201801115. [Epub ahead of print] PubMed PMID: 29714402.

8: Perna AF, Anishchenko E, Vigorito C, Zacchia M, Trepiccione F, D'Aniello S, Ingrosso D. Zebrafish, a Novel Model System to Study Uremic Toxins: The Case for the Sulfur Amino Acid Lanthionine. Int J Mol Sci. 2018 Apr 29;19(5). pii: E1323. doi: 10.3390/ijms19051323. PubMed PMID: 29710830; PubMed Central PMCID: PMC5983689.

9: Li Q, Montalban-Lopez M, Kuipers OP. Increasing the Antimicrobial Activity of Nisin-Based Lantibiotics against Gram-Negative Pathogens. Appl Environ Microbiol. 2018 May 31;84(12). pii: e00052-18. doi: 10.1128/AEM.00052-18. Print 2018 Jun 15. PubMed PMID: 29625984; PubMed Central PMCID: PMC5981070.

10: Dolle AB, Jagadeesh N, Bhaumik S, Prakash S, Biswal HS, Gowd KH. Electron transfer dissociation of synthetic and natural peptides containing lanthionine/methyllanthionine bridges. Rapid Commun Mass Spectrom. 2018 Jun 15;32(11):831-843. doi: 10.1002/rcm.8108. PubMed PMID: 29520895.

11: Montalbán-López M, Deng J, van Heel AJ, Kuipers OP. Specificity and Application of the Lantibiotic Protease NisP. Front Microbiol. 2018 Feb 9;9:160. doi: 10.3389/fmicb.2018.00160. eCollection 2018. PubMed PMID: 29479343; PubMed Central PMCID: PMC5812297.

12: Koehler D, Shah ZA, Hensley K, Williams FE. Lanthionine ketimine-5-ethyl ester provides neuroprotection in a zebrafish model of okadaic acid-induced Alzheimer's disease. Neurochem Int. 2018 May;115:61-68. doi: 10.1016/j.neuint.2018.02.002. Epub 2018 Feb 21. PubMed PMID: 29475037; PubMed Central PMCID: PMC5865644.

13: Ogasawara Y, Dairi T. Peptide Epimerization Machineries Found in Microorganisms. Front Microbiol. 2018 Feb 6;9:156. doi: 10.3389/fmicb.2018.00156. eCollection 2018. Review. PubMed PMID: 29467749; PubMed Central PMCID: PMC5808125.

14: Kakkar N, Perez JG, Liu WR, Jewett MC, van der Donk WA. Incorporation of Nonproteinogenic Amino Acids in Class I and II Lantibiotics. ACS Chem Biol. 2018 Apr 20;13(4):951-957. doi: 10.1021/acschembio.7b01024. Epub 2018 Feb 21. PubMed PMID: 29439566; PubMed Central PMCID: PMC5910287.

15: Cichero E, Fresia C, Guida L, Booz V, Millo E, Scotti C, Iamele L, de Jonge H, Galante D, De Flora A, Sturla L, Vigliarolo T, Zocchi E, Fossa P. Identification of a high affinity binding site for abscisic acid on human lanthionine synthetase component C-like protein 2. Int J Biochem Cell Biol. 2018 Apr;97:52-61. doi: 10.1016/j.biocel.2018.02.003. Epub 2018 Feb 5. PubMed PMID: 29421190.

16: Wang J, Xiao Q, Chen X, Tong S, Sun J, Lv R, Wang S, Gou Y, Tan L, Xu J, Fan C, Ding G. LanCL1 protects prostate cancer cells from oxidative stress via suppression of JNK pathway. Cell Death Dis. 2018 Feb 7;9(2):197. doi: 10.1038/s41419-017-0207-0. PubMed PMID: 29416001; PubMed Central PMCID: PMC5833716.

17: Clemens R, Zaschke-Kriesche J, Khosa S, Smits SHJ. Insight into Two ABC Transporter Families Involved in Lantibiotic Resistance. Front Mol Biosci. 2018 Jan 22;4:91. doi: 10.3389/fmolb.2017.00091. eCollection 2017. Review. PubMed PMID: 29404338; PubMed Central PMCID: PMC5786555.

18: Shen D, Hensley K, Denton TT. Multiple-step, one-pot synthesis of 2-substituted-3-phosphono-1-thia-4-aza-2-cyclohexene-5-carboxylates and their corresponding ethyl esters. Bioorg Med Chem Lett. 2018 Feb 15;28(4):562-565. doi: 10.1016/j.bmcl.2018.01.052. Epub 2018 Feb 1. PubMed PMID: 29398540; PubMed Central PMCID: PMC5817002.

19: Both EB, Shao S, Xiang J, Jókai Z, Yin H, Liu Y, Magyar A, Dernovics M. Selenolanthionine is the major water-soluble selenium compound in the selenium tolerant plant Cardamine violifolia. Biochim Biophys Acta. 2018 Jan 10. pii: S0304-4165(18)30006-0. doi: 10.1016/j.bbagen.2018.01.006. [Epub ahead of print] PubMed PMID: 29331509.

20: Jeong JH, Ha SC. Crystal Structure of NisI in a Lipid-Free Form, the Nisin Immunity Protein, from Lactococcus lactis. Antimicrob Agents Chemother. 2018 Feb 23;62(3). pii: e01966-17. doi: 10.1128/AAC.01966-17. Print 2018 Mar. PubMed PMID: 29311076; PubMed Central PMCID: PMC5826101.