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Key Documents

L8543

Sigma-Aldrich

DL-Lanthionine

≥98% (TLC)

Synonyma:

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

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About This Item

Empirický vzorec (Hillův zápis):
C6H12N2O4S
Číslo CAS:
3183-08-2
Molekulová hmotnost:
208.24
EC Number:
221-676-5
UNSPSC Code:
12352209
NACRES:
NA.26

product name

DL-Lanthionine, ≥98% (TLC)

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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Související kategorie

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
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Osvědčení o analýze (COA)

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Sigma-Aldrich

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Bactenecin ≥95% (HPLC)

Sigma-Aldrich

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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
Steffen F Hansen et al.
Journal of dairy science, 103(7), 5874-5881 (2020-05-12)
During heat treatment of milk, β-lactoglobulin (β-LG) associates with the milk fat globule membrane (MFGM). The objective of this study was to examine different binding types that could be involved in this process. First, we tested the thiol-disulfide bond interchange
Autocrine abscisic acid mediates the UV-B-induced inflammatory response in human granulocytes and keratinocytes.
Bruzzone S, Basile G, Mannino E, et al.
Journal of Cellular Physiology, 227(6), 2502-2510 (2011)
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
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