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Synthesis of the tritium labelled ß‐casomorphine analogues 3 H‐Phe‐Pro‐Gly‐OH and 3 H 2 ‐Tyr‐Pro‐ 3 H‐Phe‐pyrrolidide
Author(s) -
Oehlke J.,
Born I.,
Neubert K.,
Mittag E.,
Niedrich H.
Publication year - 1991
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580291202
Subject(s) - chemistry , tritium , residue (chemistry) , stereochemistry , peptide , specific activity , cleavage (geology) , catalysis , enzyme , biochemistry , physics , geotechnical engineering , fracture (geology) , nuclear physics , engineering
The precursor peptides H‐Phe(I)‐Pro‐Gly‐OH (III) and H‐Tyr(I 2 )‐Pro‐Phe(I)‐pyrrolidide (VIII) were synthesized by stepwise elongation from the C‐terminal end and by coupling of Boc‐Tyr(I 2 )‐Pro‐OH with H‐Phe(I)‐pyrrolidide and following deprotection of the Boc‐residue respectively. Catalytic dehalotritiation yielded tritated peptides with specific radioactivities of 450 and 1500 GBq/mmol respectively. Cleavage of 3 H 2 ‐Tyr‐Pro‐ 3 H‐Phe‐pyrrolidide by dipeptidylpeptidase IV resulted in fragments with specific radioactivities of 950 ( 3 H 2 ‐Tyr‐Pro) and 590 GBq/mmol ( 3 H‐Phe‐pyrrolidide).