一种用于将氟快速引入肽和功能化药物的辅基。
A PROSTHETIC GROUP FOR THE RAPID INTRODUCTION OF FLUORINE INTO PEPTIDES AND FUNCTIONALIZED DRUGS.
作者信息
Jacobson K A, Furlano D C, Kirk K L
机构信息
Laboratory of Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, NIH, Bethesda, MD 20892 (U.S.A.).
出版信息
J Fluor Chem. 1988 Jun;39(3):339-47. doi: 10.1016/S0022-1139(00)81606-1. Epub 2001 Mar 1.
Abstract
Fluoride ion as the tetrabutylammonium salt displaces bromide in para-substituted benzyl bromides in acetonitrile or dimethylformamide. The p-bromomethyl benzoyl (BMB) group has been coupled to amino groups, including peptide amino groups, via its N-hydroxysuccinimide ester. In a subsequent step, the facile displacement of bromide by fluoride occurred under conditions compatible for use with (18)F radiotracers.
摘要
作为四丁基铵盐的氟离子在乙腈或二甲基甲酰胺中取代对取代苄基溴中的溴离子。对溴甲基苯甲酰基（BMB）基团已通过其N-羟基琥珀酰亚胺酯与氨基（包括肽氨基）偶联。在随后的步骤中，在与（18）F放射性示踪剂兼容的使用条件下，氟离子很容易取代溴离子。
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本文引用的文献
1
N-hydroxysulfosuccinimide active esters: bis(N-hydroxysulfosuccinimide) esters of two dicarboxylic acids are hydrophilic, membrane-impermeant, protein cross-linkers.
Biochemistry. 1982 Aug 17;21(17):3950-5. doi: 10.1021/bi00260a008.
2
Aromatic retinoic acid analogues. 2. Synthesis and pharmacological activity.
J Med Chem. 1983 Sep;26(9):1282-93. doi: 10.1021/jm00363a013.
3
Visual methods for the nanomolar detection of electrophilic reagents.
J Biochem Biophys Methods. 1983 Nov;8(3):213-22. doi: 10.1016/0165-022x(83)90069-6.
4
Aromatic radiofluorination with [18F]fluorine gas: 6-[18F]fluoro-L-dopa.
J Nucl Med. 1984 Nov;25(11):1228-33.
5
A new high affinity, iodinated adenosine receptor antagonist as a radioligand/photoaffinity crosslinking probe.
Mol Pharmacol. 1987 Aug;32(1):184-8.
6
8-Substituted xanthines as antagonists at A1- and A2-adenosine receptors.
Biochem Pharmacol. 1988 Oct 1;37(19):3653-61. doi: 10.1016/0006-2952(88)90398-x.
7
Functionalized congeners of adenosine: preparation of analogues with high affinity for A1-adenosine receptors.
J Med Chem. 1985 Sep;28(9):1341-6. doi: 10.1021/jm00147a039.
8
Radiosynthesis of [18F]3-acetylcyclofoxy: a high affinity opiate antagonist.
Int J Appl Radiat Isot. 1985 Jun;36(6):429-33. doi: 10.1016/0020-708x(85)90204-2.
9
[Reagents for modifying proteins and nucleic acids. Synthesis of glyoxal- and bromacyl-containing amides of dinucleotides].
Dokl Akad Nauk SSSR. 1977;236(4):1022-4.
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