Thiohydantoins. I. The Preparation of Some 2-Thiohydantoins from Amino Acids and Acylamino Acids

1952 ◽  
Vol 5 (4) ◽  
pp. 711 ◽  
Author(s):  
JM Swan
Keyword(s):  
Amino Acids ◽  
Acetic Anhydride ◽  
Ammonium Thiocyanate ◽  
Acyl Derivatives ◽  
Degradation Of Peptides

A reinvestigation of the stepwise degradation of peptides and proteins by the Schlack and Kumpf (1926) procedure, which involves conversion of the terminal carboxyl residue to a 5-substituted-2-thiohydantoin; has been undertaken. The following amino acids or their aoetyl derivatives have been converted by warming with acetic anhydride and ammonium thiocyanate into the corresponding 1-acetyl-2-thio-hydantoins: valine, methionine, isoleucine, α-aminophenylacetic acid, tryptophane, histidine, and tyrosine. These new 1-acetyl-2-thiohydantoins, as well as others, have been deacetylated by an improved procedure. Certain 1-acyl-5-carbethoxy-2-thio- hydantoins on hydrolysis give 2-thiohydantoin only. N-acetylthreonine, acetic anhydride, and ammonium thiocyanate produce 5-ethylidene-2-thiohydantoin, also obtained by the condensation of acetaldehyde with 2-thiohydantoin or its 1-acyl derivatives, or from the interaction of ammonium thiocyanate with 2-phenyl-4-ethylideneoxazol-5-one. This type of rearrangement occurs in other cases.

Thiohydantoins. II. Thiohydantoins Derived from Aspartic and Glutamic Acids

1952 ◽  
Vol 5 (4) ◽  
pp. 721
Author(s):  
JM Swan
Keyword(s):  
Acetic Anhydride ◽  
Carboxylic Acids ◽  
Ammonium Thiocyanate ◽  
Derivatives Of ◽  
Isomeric Pairs ◽  
Acyl Derivatives

N-Acyl derivatives of the &carboxylic acids, aspartic and glutamic acids, yield the corresponding anhydrides when heated with acetic anhydride in the presence or absence of ammonium thiocyanate. In general these anhydrides form isomeric pairs of amides and anilides, and only one of each pair can be converted into the corresponding 2-thiohydantoin. The anhydrides from N-phenylacetyl- and N-p-nitro-benzoylglutamic acids, and N-acetylaspartic acid have been regarded hitherto as oxazolones.

Studies in Thiohydantoin Chemistry. I. Some Aspects of the Schlack-Kumpf Reaction

1996 ◽  
Vol 49 (5) ◽  
pp. 541 ◽  
Author(s):  
BM Duggan ◽  
RL Laslett ◽  
JFK Wilshire
Keyword(s):  
Amino Acids ◽  
Acetic Acid ◽  
Acetic Anhydride ◽  
Ammonium Thiocyanate ◽  
Sodium Thiocyanate ◽  
Side Chains ◽  
Derivatives Of

An investigation has been carried out into the Schlack-Kumpf reaction, i.e., the reaction of amino acids with a mixture of acetic anhydride, acetic acid and sodium thiocyanate (occasionally ammonium thiocyanate was used). Particular emphasis was placed on the reactions with amino acids containing sensitive or functional side chains, i.e., serine, threonine , arginine , proline , lysine, histidine , cysteine , and aspartic and glutamic acids. The reaction of serine, and of certain of its O- and N-substituted derivatives, takes an unusual course to give an acetylated thiohydantoin derivative of cysteine. Correspondingly, threonine gives an acetylated thiohydantoin derivative of β- methylcysteine. Similar reactions occurred with the 3-phenylthiohydantoin derivatives of serine and of threonine to give acetylated thiohydantoin derivatives of cysteine and of β-methylcysteine respectively.

ChemInform Abstract: N-ACYL DERIVATIVES OF ORGANOPHOSPHORUS ANALOGS OF AMINO ACIDS, THEIR ESTERS AND AMIDES

1980 ◽  
Vol 11 (15) ◽  
Author(s):  
N. B. TARUSOVA ◽  
I. A. GANDURINA ◽  
YU. N. ZHUKOV ◽  
G. M. YAKOVLEVA ◽  
R. M. KHOMUTOV
Keyword(s):  
Amino Acids ◽  
Derivatives Of ◽  
Acyl Derivatives

N-acyl derivatives of organophosphorus analogs of amino acids, their esters, and amides

1979 ◽  
Vol 28 (7) ◽  
pp. 1475-1478
Author(s):  
N. B. Tarusova ◽  
I. A. Gandurina ◽  
Yu. N. Zhukov ◽  
G. M. Yakovleva ◽  
R. M. Khomutov
Keyword(s):  
Amino Acids ◽  
Derivatives Of ◽  
Acyl Derivatives

Preparation of some long-chain N-acyl derivatives of essential amino acids for nutritional studies

1980 ◽  
Vol 58 (7) ◽  
pp. 573-576 ◽  
Author(s):  
Alenka Paquet
Keyword(s):  
Amino Acids ◽  
Fatty Acids ◽  
Physical Properties ◽  
Essential Amino Acids ◽  
Nutritional Studies ◽  
Derivatives Of ◽  
Acyl Derivatives ◽  
Long Chain

Long-chain N-acyl derivatives of methionine, tryptophan, threonine, and lysine (N6) have been obtained by the reaction of succinimidyl esters of fatty acids with the unprotected amino acids. Their physical properties have been characterized.

Thiohydantoins. III. Anhydride Intermediates in the Formation of 1-Acyl-2-thiohydantoins from Acylamino Acids

1952 ◽  
Vol 5 (4) ◽  
pp. 728
Author(s):  
JM Swan
Keyword(s):  
Carbon Dioxide ◽  
Acetic Acid ◽  
Acetic Anhydride ◽  
Hippuric Acid ◽  
Ammonium Thiocyanate ◽  
High Yield ◽  
Mixed Anhydride

Linear anhydrides are formed by the action of acetic anhydride on p-toluene-sulphonylglycine and carbobenzyloxy-glycine, -phenylalanine, and -β-alanine. The anhydrides from the first two acids yield the corresponding 2-thiohydantoin with ammonium thiocyanate in acetic acid. Other methods for the preparation of l-p-toluenesulphonylglycine anhydride, and its 2-thiohydantoin, are also given. Hippuric acid, with ethyl chlorocarbonate and triethylamine yields ethyl hippurate, probably via the mixed anhydride and 2-phenyloxazol-5-one. The inclusion of ammonium thiocyanate gives 1-benzoyl-2-thiohydantoin in high yield. The N-carboxy anhydride of phenylalanine (4-benzyloxazolid-2,5-dione) also reacts with ammonium thiocyanate to give carbon dioxide and 5-benzyl-2-thiohydantoin.

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