Addressing Chirality in the Structure and Synthesis of [~(18)F]_5-Fluoroaminosuberic Acid ([~(18)F]FASu)

Hua Yang; Brian Tam; Milena ?olovi?; Lily Southcott; Helen Merkens; Fran?ois Bénard; Paul Schaffer

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Addressing Chirality in the Structure and Synthesis of [~(18)F]_5-Fluoroaminosuberic Acid ([~(18)F]FASu)

机译：[〜（18）f] _5-氟氨酰磺酸的结构和合成中的患者（[〜（18）f] fasu）

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An increasing number of positron emission tomography (PET) radiotracers are being developed that are modelled on various amino acids to better understand disease in a manner that is complementary to traditional glycolysis-targeting [~(18)F]-fluorodeoxyglucose. Since chiral centers are ubiquitous in amino acids, generating an optically pure radiolabeled amino acid is important for patient dose, image quality and understanding the physiology behaviour. Past studies on the radiosynthesis of amino acid radiotracers seldom address the impact of reaction conditions on their chirality. The amino acid PET tracer, [~(18)F]5-fluoroaminosuberic acid ([~(18)F]FASu), has two chiral centers at the 2-and 5-positions and is being developed as a specific tracer for the cystine transporter (system xC -), a biomarker for oxidative stress. Herein we report a method for synthesizing pure 2S,5R/S-FASu. We have resolved the 5-position configuration by applying Mosher's method combined with 2D NMR, which has enabled the synthesis of ~(18)FASu with fully known configuration. Our study serves as an example of a systematic method to identify and characterize amino acid tracers with chiral centers.

机译：正在开发越来越多的正电子发射断层扫描器（PET）放射体制酶，其在各种氨基酸上建模以更好地以与传统糖酵解靶向互补的方式更好地了解疾病[〜（18）F] -fluorodox亚葡萄糖。由于手性中心在氨基酸中普遍存在，因此产生光学纯粹的放射性标记的氨基酸对于患者剂量，图像质量和理解生理行为是重要的。过去关于氨基酸放射体制箱的可热化的研究很少地解决反应条件对其性儿的影响。氨基酸PET示踪剂[〜（18）F] 5-氟代氨磺酸（[〜（18）F] Fasu），在2-and 5-位置具有两个手性中心，并且正在开发为特定示踪剂胱氨酸转运蛋白（系统XC - ），一种用于氧化应激的生物标志物。在此，我们报告了一种用于合成纯2s，5r / s-fasu的方法。我们通过应用Mosher的方法与2D NMR组合解决了5位配置，这使得具有完全已知的配置的〜（18）Fasu的合成。我们的研究是系统方法的实例，用于识别和表征具有手性中心的氨基酸示踪剂。

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来源
《Chemistry: A European journal》 |2017年第46期|共8页
作者
Hua Yang; Brian Tam; Milena ?olovi?; Lily Southcott; Helen Merkens; Fran?ois Bénard; Paul Schaffer;
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作者单位

Life Sciences TRIUMF 4004 Wesbrook Mall V6T 2A3 Vancouver (Canada);

Life Sciences TRIUMF 4004 Wesbrook Mall V6T 2A3 Vancouver (Canada);

The British Columbia Cancer Agency 675 West 10thAve. V5Z 1L3 Vancouver (Canada);

Life Sciences TRIUMF 4004 Wesbrook Mall V6T 2A3 Vancouver (Canada);

The British Columbia Cancer Agency 675 West 10thAve. V5Z 1L3 Vancouver (Canada);

The British Columbia Cancer Agency 675 West 10thAve. V5Z 1L3 Vancouver (Canada);

Life Sciences TRIUMF 4004 Wesbrook Mall V6T 2A3 Vancouver (Canada);

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原文格式 PDF
正文语种 eng
中图分类应用化学;
关键词
amino acids; fluorine-18; chirality; cystine transporter; positron emission tomography;

机译：氨基酸;氟-18;手性;胱氨酸转运蛋白;正电子发射断层扫描;

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1. Addressing Chirality in the Structure and Synthesis of [~(18)F]_5-Fluoroaminosuberic Acid ([~(18)F]FASu) [J] . Hua Yang, Brian Tam, Milena ?olovi?, Chemistry: A European journal . 2017,第46期

机译：[〜（18）f] _5-氟氨酰磺酸的结构和合成中的患者（[〜（18）f] fasu）
2. Automated synthesis of N N ‐(2‐[ 18 18 F]Fluoropropionyl)‐ l l ‐glutamic acid as an amino acid tracer for tumor imaging on a modified [ 18 18 F]FDG synthesis module [J] . Liu Shaoyu, Sun Aixia, Zhang Zhanwen, Journal of Labelled Compounds and Radiopharmaceuticals . 2017,第7期

机译：N N - （2- [18 18 F]氟丙丙基） - L L-乙酸作为氨基酸示踪剂的自动合成，用于肿瘤成像在修饰的[18 18 F] FDG合成模块上
3. Synthesis of chiral diaza 18-crown-6 ethers from chiral amines and molecular recognition of potassium and sodium salts of amino acids [J] . Demirel N., Bulut Y. Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 2003,第17期

机译：由手性胺合成手性二氮杂18-冠-6醚及氨基酸钾钠盐的分子识别
4. Synthesis methodology,acidity and catalytic behaviour of the 18 X 10 member ring pores ITQ-33 zeolite [C] . Manuel Moliner, Maria J.Diaz-Cabanas, Vicente Fornes International Federation of European Zeolite Associations Conference . 2008

机译：合成方法，18×10成员环的酸度和催化行为孔ITQ-33沸石
5. I. Studies toward a phosphorus-based chiral auxiliary. II. N-tetrachlorophthaloyl (TCP) for ready protection/deprotection of amino sugar glycosides. III. Total synthesis of NodRf-III (C18:1)(MeFuc). [D] . Debenham, John Steele. 1997

机译：I.对磷基手性助剂的研究。二。 N-四氯邻苯二甲酰（TCP）用于氨基糖苷的保护/脱保护。三， NodRf-III（C18：1）（MeFuc）的全合成。
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机译：基于（+）-（18-Crown-6）-231112-四羧酸和（R）-或（S）-1-（1-萘基）乙胺的两个新的非对映异构手性固定相的制备和手性束缚基团对手性识别的影响
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机译：有机硼烷的手性合成。 18.选择性削减。 43. Diisopinocampheylchloroborane作为一种优良的手性还原剂，用于合成高对映体纯度的卤代醇。高度对映选择性合成

Addressing Chirality in the Structure and Synthesis of [~(18)F]_5-Fluoroaminosuberic Acid ([~(18)F]FASu)

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