Über die Hydrolyse von Wolle durch Natriumsulfid. II. Mitteilung.

Kuster, W. C.; Irion, Wilhelm

doi:10.1515/bchm2.1929.184.5.225

Cited by 22 publications

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“…The chemistry of the sulfide amino acid, lanthionine, and the mechanism of its formation from the cystine of proteins under alkaline conditions (see citations in Friedman, 1973) have been followed with special interest in our laboratory where this amino acid was first correctly characterized and named lanthionine [Horn et al, 1941;1942a,b; the structure was verified by synthesis (du Vigneaud and Brown, 1941); L-lanthionine derivatives were synthesized by selective desulfurization by tris(diethylamino)phosphine (Harpp and Gleason, 1971)]. Lanthionine had been previously reported (Küster and Irion, 1929) as an artifact of the alkaline treatment of wool but it was incorrectly identified. Lanthionine occurs naturally as a free amino acid in chick embryo (Sloane and Untch, 1966) and in plant pollen (Rossetti, 1966), as a constituent of insect haemolymph (Rao et al, 1967), and in the antibiotics subtilisin (Lewis and Snell, 1951) and nisin (Gross and Morell, 1970).…”

Section: Discussionmentioning

confidence: 99%

Amino acid analyzer studies of the products of peroxide oxidation of cystine, lanthionine, and homocystine

Lipton¹,

Bodwell²,

Jr.³

1977

J. Agric. Food Chem.

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Mixtures of several sulfur amino acid oxidation products were formed in the oxidation of cystine, lanthionine, or homocystine by aqueous hydrogen peroxide in the presence of hydrochloric acid. After 10 min at 100 "C in 6% HzOz and 0.8 N HC1, cysteic acid was the main oxidation product of cystine; lanthionine sulfoxide, lanthionine sulfone, and unidentified products were also formed. In a similar oxidation of lanthionine, lanthionine sulfoxide was the most abundant product; cysteic acid, lanthionine sulfone, and unidentified products were also formed. An identical oxidation of homocystine afforded homolanthionine sulfoxide as the main product; homolanthionine sulfone and homocysteic acid were also formed. When homocystine was oxidized at 50 "C, homolanthionine was the principal product. However, when the HC1 concentration was increased to 4.8 N, homocysteic acid and homolanthionine sulfone were the main products. Sulfoxide produds were distinguished by reduction with dimethyl sulfide in the presence of HC1. Thus, they were converted into their corresponding sulfides and shifted to new chromatographic locations. These desulfurizations by hydrogen peroxide in the presence of HC1 are discussed in relation to known chemical changes of amino acids, including lanthionine formation, which occur in alkali-treated foods and to the use of peroxide in food technology.

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Section: Discussionmentioning

confidence: 99%

Amino acid analyzer studies of the products of peroxide oxidation of cystine, lanthionine, and homocystine

Lipton¹,

Bodwell²,

Jr.³

1977

J. Agric. Food Chem.

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Azlactones

Carter

2011

Organic Reactions

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Azlactones may be considered the anhydrides of alpha‐acylamino acids. It is convenient to classify them into two groups, saturated and unsaturated, since the two types show characteristic differences in properties, Azlactones have been of interest mainly as intermediates in the synthesis of other compounds. Saturated azlactones are obtained most often from the corresponding amino acids used in preparing derivatives of those amino acids. Unsaturated azlactones, on the other hand, usually are prepared by condensing an aldehyde with an acylglycine and are used in the synthesis of the corresponding amino and keto acids. Four methods by which azlactones are prepared are discussed in this chapter.

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1953

Chemistry of Heterocyclic Compounds: A Series of Monographs

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Über die Hydrolyse von Wolle durch Natriumsulfid. II. Mitteilung.

Cited by 22 publications

References 0 publications

Amino acid analyzer studies of the products of peroxide oxidation of cystine, lanthionine, and homocystine

Amino acid analyzer studies of the products of peroxide oxidation of cystine, lanthionine, and homocystine

Azlactones

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