Amino Acid Analyzer Studies of the Products of Peroxide Oxidation of Cystine, Lanthionine, and Homocystine

Lipton, S. H.; Bodwell, C. E.; Jr., Albert H. Coleman,

doi:10.1021/jf60213a064

Cited by 5 publications

(6 citation statements)

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“…1), most of which are unknown. The formation of unknown oxidation products by peroxide treatment of lanthionine has been reported by others (18).…”

Section: Discussionsupporting

confidence: 55%

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Composition of peptidoglycans in Bacteroidaceae: determination and distribution of lanthionine

Vasstrand¹,

Jensen²,

Miron³

et al. 1982

Infect Immun

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Peptidoglycans of organisms belonging to the strictly anaerobic family Bacteroidaceae were investigated for the presence of lanthionine. Different procedures for the quantitation of lanthionine were compared. Performic acid and peroxide oxidation procedures on 35S-labeled peptidoglycan from Fusobacterium nucleatum Fev1 resulted in low yields of cysteic acid (42 and 60%, respectively) and many other additional unidentified oxidation products. Lanthionine was, however, recovered in high yield (89% or more) from acid hydrolysates of unoxidized peptidoglycans. Lanthionine was found exclusively in some species of Fusobacterium, in particular F. nucleatum, F. necrophorum, F. russi, and F. gonidiaformans, for which lanthionine may be ascribed a function as a taxonomic marker. Peptidoglycans of these bacteria are thus proposed to belong to a new chemotype, assigned A1 delta. One strain of Fusobacterium, F. mortiferum VPI 0473 contained both lanthionine and diaminopimelic acid in about equal proportions. Species of F.plauti had a composition atypic of gram-negative cells. Chemotypic differences were also indicated among the species of Bacteroides investigated. Thus, some species contained lysine and not diaminopimelic acid as the major dibasic amino acid (e.g., F. asaccharolyticus). It is concluded that peptidoglycans of gram-negative organisms constitute a somewhat more heterogeneous group than hitherto assumed.

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“…1), most of which are unknown. The formation of unknown oxidation products by peroxide treatment of lanthionine has been reported by others (18).…”

Section: Discussionsupporting

confidence: 55%

“…The identity of peak II compounds eluted at the retention times expected for lanthionine sulfoxide (as a split peak at 48 and 53 min) and lanthionine sulfone (at 61 min). The identification of these peaks was based on the work of Lipton et al (18).…”

Section: Resultsmentioning

confidence: 99%

Composition of peptidoglycans in Bacteroidaceae: determination and distribution of lanthionine

Vasstrand¹,

Jensen²,

Miron³

et al. 1982

Infect Immun

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“…It was also clearly demonstrated (Table 3) that increased purity of carnocin UI49 caused decreased stability to heating and storage at higher temperature. This work presents strong evidence for the presence of lanthionine in carnocin U149. Upon amino acid analysis, a chromatographic peak in front of glycine was detected in the same position as that found for lanthionine (20). Amino acid analysis of performic acid-oxidized bacteriocin revealed the presence of cysteic acid in the hydrolysate, as is also found when lanthionine is oxidized (20).…”

Section: Discussionsupporting

confidence: 53%

“…It is known that lanthionine migrates at that position, and, by control analysis, with lanthionine as a standard, it was confirmed that the unidentified peak eluted at the same position as lanthionine (data not shown). Upon oxidation with performic acid, lanthionine is hydrolyzed into a cysteic acid residue (20). By exposing carnocin UI49 to this treatment, amino acid analysis revealed one to two residues of cysteic acid per bacteriocin molecule, indicating the presence of lanthionine or lanthionine derivatives in the bacteriocin molecule.…”

Section: Resultsmentioning

confidence: 99%

Purification and characterization of a new bacteriocin isolated from a Carnobacterium sp

Stoffels

Nissen‐Meyer

Guðmundsdóttir

et al. 1992

Appl Environ Microbiol

113

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A bacteriocin-producing Carnobacterium sp. was isolated from fish. The bacteriocin, termed carnocin UI49, was purified to homogeneity by a four-step purification procedure, including hydrophobic interaction chromatography and reverse-phase chromatography. Carnocin U149 has a bactericidal mode of action. It was shown to be heat tolerant and stable between pH 2 and 8. At pH above 8, carnocin UI49 was rapidly inactivated. Amino acid analysis revealed a composition of about 35 to 37 amino acids in addition to an unidentified peak which migrates at the position of lanthionine. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis analysis suggests a molecular weight of about 4,500 to 5,000. Mass spectrometry gave a molecular weight of 4,635, which is about 1,000 larger than that calculated from the amino acid analysis data. Performic acid oxidation of carnocin UI49, followed by amino acid hydrolysis, revealed the presence of cysteic acid. The sequence of the first seven amino acid residues was determined to be N-Gly-Ser-Glu-Ile-Gln-Pro-Arg. After the seventh amino acid, carnocin UI49 was not available for further Edman degradation. The results suggest that carnocin U149 belongs to the class of bacteriocins termed lantibiotics.

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“…Usually, L-cysteic acid was prepared from the oxidation of L-cystine in HCl solution with bromine (Clarke, 1966) or hydrogen peroxide (Lipton et al, 1977) as oxidizing reagent. The oxidation of L-cystine with dimethyl sulfoxide under the catalysis of I 2 -HCl can give L-cysteic acid (Lowe, 1977).…”

Section: Introductionmentioning

confidence: 99%

Efficient preparation of L-cysteic acid and its esters

Tao

Luo

et al. 2004

Amino Acids

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Amino Acid Analyzer Studies of the Products of Peroxide Oxidation of Cystine, Lanthionine, and Homocystine

Cited by 5 publications

References 0 publications

Composition of peptidoglycans in Bacteroidaceae: determination and distribution of lanthionine

Composition of peptidoglycans in Bacteroidaceae: determination and distribution of lanthionine

Purification and characterization of a new bacteriocin isolated from a Carnobacterium sp

Efficient preparation of L-cysteic acid and its esters

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