Condensation of Proteins With Thiocyanate

Haurowitz, Felix; Zimmerman, M.D.; Hardin, Richard L.; Lisie, Sarah G.; Horowitz, Jack; Lietze, Arthur; F, Bursa

doi:10.1016/s0021-9258(18)64975-0

Cited by 10 publications

(1 citation statement)

References 35 publications

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“…The absorbancy measured at 280 m/i was virtually identical with that calculated for complete reaction of the carboxyl terminus, assuming en 1300 for each of the 3 tyrosine residues and cm 17,500 for the acylthiohydantoin. Haurowitz et al (1957), using radioactive ammonium thiocyanate, had shown previously that one to two NCS residues per molecule were incorporated into insulin, ribonuclease, chymotrypsin, and lysozyme, consistent with a good yield of carboxylterminal thiohydantoin and little reaction elsewhere.…”

Section: Resultsmentioning

confidence: 62%

Determination of the carboxyl termini of proteins with ammonium thiocyanate and acetic anhydride, with direct identification of the thiohydantoins

Cromwell

Stark

1969

Biochemistry

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Section: Resultsmentioning

confidence: 62%

Determination of the carboxyl termini of proteins with ammonium thiocyanate and acetic anhydride, with direct identification of the thiohydantoins

Cromwell

Stark

1969

Biochemistry

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α-Thioureidoalkylation of urea heteroanalogs

et al. 2009

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α Thioureidoalkylation of urea heteroanalogs such as thiosemicarbazide, amino guanidine, sulfamide, and sulfonamides with 4,5 dihydroxyimidazolidine 2 thiones has been studied. Previously unknown 4,5 bis[thiosemicarbazido(guanidinoamino)]imidazolidine 2 thiones, 5,7 dialkylperhydroimidazo[4,5 e] [1,2,4]triazine 3,6 dithiones, 4,6 diethyl 5(3H) thioxotetrahydro 1H imidazo[4,5 c][1,2,5]thiadiazole 2,2 dioxide, and 1,3 dialkyl 4 [guanidinoimino(arylsulfonylimino)]imidazolidine 2 thiones have been synthesized. Key words: α thioureidoalkylation, thiosemicarbazide, aminoguanidine, sulfamide, 4,5 dihydroxyimidazolidine 2 thiones, 4,5 bis[thiosemicarbazido(guanidinoamino)]imidazol idine 2 thiones, 5,7 dialkylperhydroimidazo[4,5 e][1,2,4]triazine 3,6 dithiones, 4,6 diethyl 5(3H) thioxotetrahydro 1H imidazo[4,5 c][1,2,5]thiadiazole 2,2 dioxide, 1,3 dialkyl 4 [guanidinoimino(arylsulfonylimino)]imidazolidine 2 thiones.α Ureidoalkylation of ureas and their analogs with 4,5 dihydroxyimidazolidin 2 ones have been carefully studied in our laboratories. 1-5 α Ureidoalkylation of thiosemicarbazide, aminoguanidine, and sulfamides yielded 5,7 dialkyl 3 thioxoperhydroimidazo[4,5 e][1,2,4]tri azin 6 ones (1), 2 4,5 bis(thiosemicarbazido) and 4,5 bis (guanidinoamino)imidazolidin 2 ones (2, 3), 2 4 (guani dinoamino) and 4 (sulfonylimino)imidazolidin 2 ones (4-6), 2-4 and 5(3H) thioxotetrahydro 1H imidazo[4,5 c] [1,2,5]thiadiazole 2,2 dioxides (7). 5 Only few examples of the synthesis of glycoluril heteroanalogs by condensation of ureas with 4,5 dihydroxy imidazolidine 2 thiones (DHIT) have been published. 6,7The present work is devoted to α thioureidoalkylation of urea heteroanalogs (thiosemicarbazide, aminoguani dine, sulfamide, and sulfonamides) with DHIT 8a-c and development of the synthetic methods towards novel imidazolidine 2 thione derivatives.Thioureidoalkylation of thiosemicarbazide with DHIT 8a-c under conditions described previously 2 for the syn thesis of compounds 2 (water, pH 2, 80 °C, DHIT : thio semicarbazide = 1 : 2) resulted in 4,5 bis(thiosemi carbazido)imidazolidine 2 thiones 9a-c in 70-75% yields and perhydroimidazo[4,5 e][1,2,4]triazine 3,6 di thiones 10a-c (Scheme 1). Imidazotriazines 10b,c were isolated in 5-15% yields. Together with signals of the main product 9a, the signals that were attributed to com X = S (2), NH 2 + Cl -(3)pound 10a (4.94 and 5.25 (both d, each 1 H, CH-CH, J = 8.5 Hz); 5.69 (br.s, 1 H, NH); 7.29 (br.s, 2 H, 2 NH);

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Chemical procedures for C-terminal sequencing of peptides and proteins

Inglis¹

1991

Analytical Biochemistry

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Condensation of Proteins With Thiocyanate

Cited by 10 publications

References 35 publications

Determination of the carboxyl termini of proteins with ammonium thiocyanate and acetic anhydride, with direct identification of the thiohydantoins

Determination of the carboxyl termini of proteins with ammonium thiocyanate and acetic anhydride, with direct identification of the thiohydantoins

α-Thioureidoalkylation of urea heteroanalogs

Chemical procedures for C-terminal sequencing of peptides and proteins

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