Synthesis of the new immunostimulating agent pidotimod (3-L-pyroglutamyl-L-thiazolidine-4-carboxylic acid) labelled with 14C- and 35S-isotopes
✍ Scribed by Patrizia Ferraboschi; Paride Grisenti; Enzo Santaniello; Claudio Giachetti; Giovanni Zanolo; Giovanni Signorelli; Germano Coppi
- Publisher
- John Wiley and Sons
- Year
- 1992
- Tongue
- French
- Weight
- 334 KB
- Volume
- 31
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
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).