Synthesis of the new immunostimulating agent pidotimod (3‐L‐pyroglutamyl‐L‐thiazolidine‐4‐carboxylic acid) labelled with 14C‐ and 35S‐isotopes
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Abstract 3‐L‐Pyroglutamyl‐L‐thiazolidine‐4‐carboxylic acid (Pidotimod), a new immunostimulating agent, has been prepared labelled with 14 C and 35 isotopes starting from L‐[U‐ 14 C]‐glutamic acid 5 and L‐[ 35 S]‐cysteine hydrochloride 6 , respectively. In the first synthesis, L‐[U‐ 14 C]‐ 5 is converted into L‐[U‐ 14 C]‐pyroglutamic acid 2 , which was reacted with ethyl L‐thiazolidine‐4‐carboxylate 3 to afford the ester 4 , in turn hydrolyzed to [ 14 C]‐Pidotimod 1 . In the second synthesis, L‐[ 35 S]‐ 6 reacted with formaldehyde to give L‐[ 35 S]‐thiazolidine‐4‐carboxylic acid 7 , which was coupled with the activated ester of pyroglutamic acid, compound 8 , to afford [ 35 S]‐Pidotimod 1 . The total activity of [ 14 C]‐Pidotimod was 1.2 mCi (specific activity 5.52 mCi/mmol) and that of [ 35 S]‐Pidotimod was 1.0 mCi (specific activity 9.43 mCi/mmol).Keywords:
Thiazolidine
Pyroglutamic acid
Hydrochloride
Details are reported for the synthesis of DL-selenazolidine-4-carboxylic acid starting from DL-selenocystine and formaldehyde. Some chemical reactions and the paper and ion-exchange chromatographic behaviour of selenazolidine carboxylic acid in comparison with thiazolidine-4-carboxylic acid are described.
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Abstract A synthesis of ( S )‐isothiazolidine‐1,1‐dioxide‐3‐carboxylic acid ( 2 ), the sulphonamido analogue of pyroglutamic acid, is reported. The protocol of its insertion into a peptide molecule, including protection and deprotection steps, is also described.
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D-Thiazolidine-4-carboxylic acid is a good substrate for hog kidney D-aminoacid oxidase. Data are presented showing that the only oxidation product is delta 3-thiazoline-4-carboxylic acid, which does not undergo further spontaneous degradation. Thus, the oxidation of D-thiazolidine-4-carboxylic acid by D-aminoacid oxidase differs considerably from the oxidation of its L-isomer catalyzed by rat liver mitochondria which gives as final product N-formylcystine, possibly through the intermediate delta 2-thiazoline-4-carboxylic acid.
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Thiazolidine
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Abstract The helical structures of poly[( S )‐thiazolidine‐4‐carboxylic acid], in the cis and trans forms, were redetermined by using the new sets of bond angles and bond lengths established by X‐ray diffraction analysis of L ‐thioproline. Calculations of the helical structures of poly‐ L ‐proline and poly[( S )‐oxazolidine‐4‐carboxylic acid] were also repeated. As a result of these energy calculations, it is suggested that, in contrast to poly‐ L ‐proline and poly[( S )‐oxazolidine‐4‐carboxylic acid], poly[( S )‐thiazolidine‐4‐carboxylic acid] should not mutarotate from the trans to the cis form. This result is due to the fact that the energy barrier for the conversion is most likely too high. Previous experimental work is consistent with this finding.
Thiazolidine
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