Syntheses, resolution optique et radiolyse d' Acides Amines Trities a Haute Activite Specifique. I - D,L-Lysine (3H-4,5,6,6); L-lysine (3H-4,4,5,5); L-Leucine (3H-4,5,5,5); Acide D-α-amino Adipique (3H-4,4,5,5); Acide γ-Amino Butyrique (3H-2,2,3,3)

✍ Scribed by Dominique Ego; Jean-Pierre Beaucourt; Louis Pichat

• Book ID: 102901067
• Publisher: John Wiley and Sons
• Year: 1986
• Tongue: French
• Weight: 611 KB
• Volume: 23
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580230302

✦ Synopsis

Ltiamino-4-heqnoic acidwas prepared from 1, 4-dichloro-2-butyne and diethyl acetamidomlomte. Tke catalytic reduction of -$ trtth tritium led t o f4,5,6,6-RI DL-lysines) spec. act. 113 Ci/mM. Tke catalytic reduction with tritium of L-2-amino-6-t-butoqcmbonytamino-4-kelcyndc acid _Z followed by hydrolysis gave [4,4,5,5- H] L-lysineg spec. act. : 120 Ci/mM.

DL-2-amino-~,5-dichtoro-4-metkyl-4-pentenoic

acid 2 was prepared from 2methyt-l,l, 3-trichloro-l-prapene mul diethgl acetamidomtonate. The o p t ical isomers were separated by preparative HPLC. The catalytic reduction of the L e m t i o m r gave p,5,5,5-H ] L-leucine -13 spec. act. 140 Ci/mM.

Ethoqcarbonylation of ethyl 2-acety~no-2-ethoxycarbmyl I-pentynoate :

i n presence of palladium gave triethyl 4-acetylamino-l-butyne-1,4, 4 -t gcarboqlate 16. Reduction ofwith t r i t i u m followed by hydrolysis gave of -18' with L-aminoddase led t o D-Q-aminoadipic a d dwith the same specific activity. kthoxycarbonyktion of 3-vhthatimido-l-propyne methyl 4-phthalimido-2-butyno66ea which t r i t i a t i a n followed by hydrol y s i s led t o [2,2,3,3-3H] GABA -2 spec. act. 109 Ci/nrM. 3H NMR anulyses were carried out i n each case. Studies on the self radiolysis of these aminoacids during storage are reported.