Peptides. Part XXI. Dehydrogenation of some thiazolines derived from cysteine

Barton, Moira A.; Kenner, G. W.; Sheppard, R. C.

doi:10.1039/j39660001061

Cited by 11 publications

(6 citation statements)

References 1 publication

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“…9 At strongly acidic conditions, 12 NAC has been observed to form a five-membered thiazolidine ring through reaction of the thiol with the amide group, which subsequently eliminates H 2 O (catalyzed by H + ) to form 2-methyl-2-thiazoline-4carboxylic acid (MTC) having a thiazoline ring. 13,14 This reaction is termed as the cyclization of NAC. A plausible intermediate in the cyclization of NAC is 2-methylthiazolidine-4-carboxylic acid (MTCA), which readily decomposes through a second-order reaction involving OH − to produce MTC.…”

Section: Introductionmentioning

confidence: 99%

Monitoring the in Vitro Thiazolidine Ring Formation of Antioxidant Drug N-Acetyl-l-cysteine at Basic pH and Detection of Reaction Intermediates: A Raman Spectroscopic and Ab Initio Study

et al. 2018

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The important cyclization reaction of antioxidant drug N-acetyl-L-cysteine (NAC) has been monitored in vitro at basic pH with the help of time series Raman spectroscopy. The thiazoline ring formation of NAC at acidic pH is a well-known reaction and has been studied extensively. However, the formation of a thiazolidine ring from NAC at basic pH has not been investigated precisely till date. The effect of basicity of the medium on the rate of cyclization has been investigated by studying the reaction at five different basic pH values. Raman signatures of cyclization have been observed with the passage of time and are found to appear faster as the basicity of the medium increases. Ab initio calculations have been done to understand the plausible mechanism of the reaction at basic pH. It is observed that formation of a thiazolidine ring from NAC occurs primarily in four steps, which involve proton abstraction from the thiol (SH) group of NAC and subsequent formation of an S−C bond by a nucleophilic attack of the C−S group on the protonated C−O−H group in NAC. Correlation of the theoretically calculated results with experimental Raman spectral analysis has led to a detailed and proper understanding of this important biochemical reaction.

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Section: Introductionmentioning

confidence: 99%

Monitoring the in Vitro Thiazolidine Ring Formation of Antioxidant Drug N-Acetyl-l-cysteine at Basic pH and Detection of Reaction Intermediates: A Raman Spectroscopic and Ab Initio Study

et al. 2018

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“…The dehydrogenation of structurally related thiazolines by quinones has been investigated by Kenner and co-workers (25) Compound 17 gives correct analytical figures, mass spectral parent peak, the i.r. confirms the absence of an aryl ketone band and the 4-vinyl proton is prominent in the n.m.r.…”

mentioning

confidence: 99%

Reaction of 3-aroylaziridines with aryl isothiocyanates

Lown¹,

Dallas²,

Maloney³

1969

Can. J. Chem.

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3-Aroylaziridines react with a variety of aryl isothiocyanates in refluxing benzene to give either (a) 4-aroyl-5-arylamino-4-thiazolines by a [2 + 31 cycloaddition and/or (b) 2-arylamino-4-aroyl-4-thiazolines.When the N-substituent of the aziridine is cyclohexyl or isopropyl the product type (a) is isolated in greater quantity, but when the N-substituent is methyl, product type (b) is isolated in greater quantity. The reactions provide convenient one-step syntheses of new 4-aroyl-4-thiazolines.

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“…La cyclisation realisee constitue d'ailleurs une excellente protection contre les degradations parasites du peptide forme. La y (-N-TFA a-ethoxy)-glutamyl-methoxycysteine ainsi obtenue est transformee aisement en une thiazoline-d2 par distillation sous vide [9].…”

Section: Syntheseunclassified

“…Nous avons utilise plusieurs procedes pour deshydrogener la thiazoline-d2 : en premier lieu, celui preconise par Barton et coll. [9], ensuite par emploi de Palladium, Selenium et Soufre. C'est I'aromatisation par le soufre B 230" qui donne les meilleurs resultats.…”

Section: Syntheseunclassified

Établissement de la Formule de Structure d'un Nouvel Acide Aminé Soufré de Xerocomus Subtomentosus

Jadot

Casimir

Warin

1969

Bulletin des Soc Chimique

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Le nouvel acide amind soufre isolt du champignon Xerocomus Subtomentosus est caracterise par la formule brute C8Hl0NZO4S. Des etudes analytiques et des reactions de degradations ont montre qu'il s'agissait d'un acide a-amin6 bibasique derivant du thiazole. I1 s'agit de I'acide a-amino y-(carboxy-4 thiazolyl-2) butyrique. La synthkse de cette. substance corrobore la structure chimique proposte du compose naturel. The new Sulfur-containing amino acid which has been isolated from the mushroom Xerocomus Subtomentosus is characterized by the general formula C8Hl0N2OpS. Analytical studies and degrading reactions have shown that it was an a-amino dibasic acid derived from thiazol : the a-amino y-[2-(4-carboxy)thiazolyl]butyric acid. The synthesis of that compound supports the chemical structure proposed for the natural compound.

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Peptides. Part XXI. Dehydrogenation of some thiazolines derived from cysteine

Cited by 11 publications

References 1 publication

Monitoring the in Vitro Thiazolidine Ring Formation of Antioxidant Drug N-Acetyl-l-cysteine at Basic pH and Detection of Reaction Intermediates: A Raman Spectroscopic and Ab Initio Study

Monitoring the in Vitro Thiazolidine Ring Formation of Antioxidant Drug N-Acetyl-l-cysteine at Basic pH and Detection of Reaction Intermediates: A Raman Spectroscopic and Ab Initio Study

Reaction of 3-aroylaziridines with aryl isothiocyanates

Établissement de la Formule de Structure d'un Nouvel Acide Aminé Soufré de Xerocomus Subtomentosus

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