Abstract
A method for the preparation of a radiolabeled CCK(A)-specific antagonist, (R)-N-pentyl-N-(4,5-di[3H]pentyl)N(α)-(3-quinolinoyl)glutamic acid amide, [3H]-A-65186, is described. (R)-γ-Benzyl-N-BOC-glutamic acid was coupled with N-(4-pentenyl)-N-pentylamine using BOPCl and TEA in dichloromethane to provide the corresponding amide. Deprotection of the α-amino moiety followed by coupling with 3-quinolinecarboxylic acid in the presence of EDCI, TEA, and HOBt in dichloromethane resulted in (R)-N-(4-pentenyl)-N-pentyl γ-benzyl-N(α)-(3-quinolinoyl)glutamic acid amide. Tritiation with concomitant hydrogenolysis of the benzyl ester proceeds smoothly to provide [3H]-A-65186.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 77-90 |
| Number of pages | 14 |
| Journal | Journal of Labelled Compounds and Radiopharmaceuticals |
| Volume | 43 |
| Issue number | 1 |
| DOIs | |
| State | Published - Jan 1 2000 |
All Science Journal Classification (ASJC) codes
- Analytical Chemistry
- Biochemistry
- Radiology Nuclear Medicine and imaging
- Drug Discovery
- Spectroscopy
- Organic Chemistry
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Cite this
Malone, J. A., Reidelberger, R. D., & Hulce, M. (2000). Synthesis of a radoilabeled type A cholecystokinin receptor antagonist, (R)-N-pentyl-N-(4,5-di[3H]pentyl)N(α)-(3-quinolinoyl)glutamic acid amide. Journal of Labelled Compounds and Radiopharmaceuticals, 43(1), 77-90. https://doi.org/10.1002/(SICI)1099-1344(200001)43:1<77::AID-JLCR292>3.0.CO;2-V