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L8543

Sigma-Aldrich

DL-Lanthionine

≥98% (TLC)

Synonym(s):

DL-3,3′-Thiodialanine, S-(2-Amino-2-carboxyethyl)-DL-cysteine

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About This Item

Empirical Formula (Hill Notation):
C6H12N2O4S
CAS Number:
Molecular Weight:
208.24
EC Number:
UNSPSC Code:
12352209
NACRES:
NA.26

product name

DL-Lanthionine, ≥98% (TLC)

Quality Level

Assay

≥98% (TLC)

form

powder

color

white

solubility

1 M HCl: soluble

application(s)

detection

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)

InChI key

DWPCPZJAHOETAG-UHFFFAOYSA-N

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Application


  • Synthesis of the lantibiotic lactocin S using peptide cyclizations on solid phase.: This research highlights innovative methods for synthesizing peptide-based antibiotics like lactocin S, utilizing dl-lanthionine to form crucial thioether crosslinks that enhance the activity and stability of these peptides (Ross et al., 2010).

  • Cystathionine gamma-lyase of Streptomyces phaeochromogenes.: This research documents the isolation and characterization of an enzyme that processes cystathionine, which involves dl-lanthionine as a structural analog, revealing its role in bacterial physiology and potential applications in biotechnology (Nagasawa et al., 1984).

  • The availability of dl-lanthionine for the promotion of growth in young rats when added to a cystine- and methionine-deficient diet.: This historical study explores the nutritional value of dl-lanthionine, investigating its ability to substitute for essential amino acids in growth diets, which helps in understanding its potential use in nutritional supplements (Jones et al., 1948).

Biochem/physiol Actions

Lanthionine is a non-typical amino acid and a monosulfide analog of cystine. Lanthionines are constituents of a group of peptide antibiotics called lantiobiotics, which include nisin and subtilin.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jun-ichi Nagao et al.
Current pharmaceutical biotechnology, 12(8), 1221-1230 (2011-04-08)
Lantibiotics are ribosomally synthesized, post-translationally modified, peptide antibiotics containing unusual amino acids such as dehydrated amino acids and lanthionine. These unusual amino acids impose conformational constraints on the peptide and contribute to the biological activity and high physicochemical stability of
Wolfgang M Müller et al.
Biochemistry, 50(39), 8362-8373 (2011-09-13)
Lantibiotics are peptide antibiotics, realizing their unique secondary structure by posttranslational modifications, the most important one being the formation of the characteristic amino acid lanthionine. Like other ribosomal peptide antibiotics, they are synthesized with an N-terminal leader peptide important for
Ayşe Ökesli et al.
Journal of the American Chemical Society, 133(34), 13753-13760 (2011-07-21)
Lantibiotics are ribosomally synthesized and post-translationally modified antimicrobial peptides that are characterized by the thioether cross-linked amino acids lanthionine (Lan) and methyllanthionine (MeLan). Cinnamycin is a 19 amino acid lantibiotic that contains one Lan and two MeLan. Cinnamycin also contains
Antonino Mavaro et al.
The Journal of biological chemistry, 286(35), 30552-30560 (2011-07-16)
Nisin is a posttranslationally modified antimicrobial peptide containing the cyclic thioether amino acids lanthionine and methyllanthionine. Although much is known about its antimicrobial activity and mode of action, knowledge about the nisin modification process is still rather limited. The dehydratase
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Bruzzone S, Basile G, Mannino E, et al.
Journal of Cellular Physiology, 227(6), 2502-2510 (2011)

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