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Synthesis of the positron-emitting radiotracer [18F]-2-fluoro-2-deoxy-d-glucose from resin-bound perfluoroalkylsulfonates

Synthesis of the positron-emitting radiotracer [18F]-2-fluoro-2-deoxy-d-glucose from resin-bound perfluoroalkylsulfonates
Synthesis of the positron-emitting radiotracer [18F]-2-fluoro-2-deoxy-d-glucose from resin-bound perfluoroalkylsulfonates
A new approach to the synthesis of 2-fluoro-2-deoxy-D-glucose (FDG, [19/18F]- 3) is described, which employs supported perfluoroalkylsulfonate precursors 33–36, where the support consists of insoluble polystyrene resin beads. Treatment of these resins with [19F]fluoride ion afforded protected FDG [19F]- 18 as the major product, and the identities of the main byproducts were determined. Acidic removal of the acetal protecting groups from [19F]- 18 was shown to produce [19F]FDG. The method has been applied to the efficient radiosynthesis of the imaging agent [18F]FDG, and was shown to produce the radiochemical tracer in good radiochemical yield (average 73%, decay corrected).
1477-0520
564-575
Brown, Lynda J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Ma, Nianchun
f911e90a-c94d-494d-812c-5a55ba99e66f
Bouvet, Denis R.
f0b8b86f-3470-42ed-95a7-4e7ac6870a22
Champion, Sue
9f8f6e1a-d1e8-4bca-93bb-029982552fb7
Gibson, Alex M.
8a1e0997-db08-45c9-9597-aca8dee8c79e
Hu, Yulai
5f6957ca-475f-42b3-892f-e2d64cf2ef11
Jackson, Alex
352997fe-a55f-4c72-8b2d-a1e951889de7
Khan, Imtiaz
472f2db0-2192-4200-b2a7-9ac4cc798fd9
Millot, Nicolas
0a6d7556-c312-4eab-8645-5c476f0e5083
Topley, Amy C.
34b283a0-f281-4750-a204-3e189ec4c48b
Wadsworth, Harry
f337a299-e45d-45d6-936e-75c88492270f
Wynn, Duncan
fa315b3a-09f6-417b-8299-f9ab7435a494
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5
Brown, Lynda J.
75aa95fa-5d27-46a7-9dbe-0f465a664f5b
Ma, Nianchun
f911e90a-c94d-494d-812c-5a55ba99e66f
Bouvet, Denis R.
f0b8b86f-3470-42ed-95a7-4e7ac6870a22
Champion, Sue
9f8f6e1a-d1e8-4bca-93bb-029982552fb7
Gibson, Alex M.
8a1e0997-db08-45c9-9597-aca8dee8c79e
Hu, Yulai
5f6957ca-475f-42b3-892f-e2d64cf2ef11
Jackson, Alex
352997fe-a55f-4c72-8b2d-a1e951889de7
Khan, Imtiaz
472f2db0-2192-4200-b2a7-9ac4cc798fd9
Millot, Nicolas
0a6d7556-c312-4eab-8645-5c476f0e5083
Topley, Amy C.
34b283a0-f281-4750-a204-3e189ec4c48b
Wadsworth, Harry
f337a299-e45d-45d6-936e-75c88492270f
Wynn, Duncan
fa315b3a-09f6-417b-8299-f9ab7435a494
Brown, Richard C.D.
21ce697a-7c3a-480e-919f-429a3d8550f5

Brown, Lynda J., Ma, Nianchun, Bouvet, Denis R., Champion, Sue, Gibson, Alex M., Hu, Yulai, Jackson, Alex, Khan, Imtiaz, Millot, Nicolas, Topley, Amy C., Wadsworth, Harry, Wynn, Duncan and Brown, Richard C.D. (2009) Synthesis of the positron-emitting radiotracer [18F]-2-fluoro-2-deoxy-d-glucose from resin-bound perfluoroalkylsulfonates. Organic & Biomolecular Chemistry, 7 (3), 564-575. (doi:10.1039/B816032e). (PMID:19156324)

Record type: Article

Abstract

A new approach to the synthesis of 2-fluoro-2-deoxy-D-glucose (FDG, [19/18F]- 3) is described, which employs supported perfluoroalkylsulfonate precursors 33–36, where the support consists of insoluble polystyrene resin beads. Treatment of these resins with [19F]fluoride ion afforded protected FDG [19F]- 18 as the major product, and the identities of the main byproducts were determined. Acidic removal of the acetal protecting groups from [19F]- 18 was shown to produce [19F]FDG. The method has been applied to the efficient radiosynthesis of the imaging agent [18F]FDG, and was shown to produce the radiochemical tracer in good radiochemical yield (average 73%, decay corrected).

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Published date: 2 February 2009

Identifiers

Local EPrints ID: 148921
URI: https://eprints.soton.ac.uk/id/eprint/148921
ISSN: 1477-0520
PURE UUID: cdbcada2-6f1d-4f19-a3c1-5bdc02ae32f0
ORCID for Lynda J. Brown: ORCID iD orcid.org/0000-0002-5678-0814
ORCID for Richard C.D. Brown: ORCID iD orcid.org/0000-0003-0156-7087

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Date deposited: 29 Apr 2010 09:42
Last modified: 20 Jul 2019 01:16

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Contributors

Author: Lynda J. Brown ORCID iD
Author: Nianchun Ma
Author: Denis R. Bouvet
Author: Sue Champion
Author: Alex M. Gibson
Author: Yulai Hu
Author: Alex Jackson
Author: Imtiaz Khan
Author: Nicolas Millot
Author: Amy C. Topley
Author: Harry Wadsworth
Author: Duncan Wynn

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