(S)-4-氟组氨酸的对映选择性合成
An Enantioselective Synthesis of (S)-4-Fluorohistidine.
作者信息
Hajduch Jan, Cramer John C, Kirk Kenneth L
机构信息
Laboratory of Bioorganic Chemistry, National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, DHHS, Bethesda, MD 20892.
出版信息
J Fluor Chem. 2008 Sep;129(9):807-810. doi: 10.1016/j.jfluchem.2008.04.011.
Abstract
We report a new synthesis of enantiomerically pure (S)-4-fluorohisitidine based on diastereoselective alkylation of MOM-protected 4-fluoro-5-bromomethyl imidazole using the Schöllkopf bis-lactim amino acid synthesis. Improvements in procedures for preparation of key intermediates are also described. (S)-4-Fluorohisitidine prepared by this new method was identical in all respects to material prepared by previous procedures.
摘要
我们报道了一种基于使用朔尔科普夫双内酰胺氨基酸合成法对甲氧基甲基（MOM）保护的4-氟-5-溴甲基咪唑进行非对映选择性烷基化反应来合成对映体纯的（S）-4-氟组氨酸的新方法。还描述了关键中间体制备程序的改进。通过这种新方法制备的（S）-4-氟组氨酸在各方面均与以前方法制备的材料相同。
相似文献
1
An Enantioselective Synthesis of (S)-4-Fluorohistidine.(S)-4-氟组氨酸的对映选择性合成
J Fluor Chem. 2008 Sep;129(9):807-810. doi: 10.1016/j.jfluchem.2008.04.011.
2
Expeditious synthesis of enantiopure, orthogonally protected bis-α-amino acids (OPBAAs) and their use in a study of Nod1 stimulation.
Chem Asian J. 2015 Feb;10(2):474-82. doi: 10.1002/asia.201403173. Epub 2014 Dec 12.
3
Enantioselective Synthesis of Arylglycines via Pd-Catalyzed Coupling of Schöllkopf Bis-Lactim Ethers with Aryl Chlorides.通过钯催化的朔尔科普夫双内酰胺醚与芳基氯的偶联反应对芳基甘氨酸进行对映选择性合成。
Angew Chem Int Ed Engl. 2023 Dec 4;62(49):e202309868. doi: 10.1002/anie.202309868. Epub 2023 Sep 26.
4
Synthesis of indan-based unusual alpha-amino acid derivatives under phase-transfer catalysis conditions.在相转移催化条件下合成茚基类特殊α-氨基酸衍生物。
J Org Chem. 2000 Mar 10;65(5):1359-65. doi: 10.1021/jo991387v.
5
Cyclopropenylcarbinol derivatives as new versatile intermediates in organic synthesis: application to the formation of enantiomerically pure alkylidenecyclopropane derivatives.环丙烯基甲醇衍生物作为有机合成中的新型通用中间体：在手性纯亚烷基环丙烷衍生物形成中的应用。
Chemistry. 2009 Aug 24;15(34):8449-8464. doi: 10.1002/chem.200901074.
6
Concise enantioselective synthesis of abscisic acid and a new analogue.脱落酸及其一种新类似物的简洁对映选择性合成
Org Biomol Chem. 2006 Nov 21;4(22):4186-92. doi: 10.1039/b611880a.
7
The Schöllkopf chiron and transition metal mediated reactions, a powerful combination for stereoselective construction of cyclic alpha-quaternary-alpha-amino acid derivatives.朔尔科普夫手性合成子与过渡金属介导的反应，是立体选择性构建环状α-季碳-α-氨基酸衍生物的有力组合。
Amino Acids. 2008 Apr;34(3):357-402. doi: 10.1007/s00726-007-0512-5. Epub 2007 May 4.
8
Dynamic kinetic transformation of sulfinyl chlorides: synthesis of enantiomerically pure C(2)-symmetric bis-sulfoxides.亚磺酰氯的动态动力学转化：对映体纯的C(2)对称双亚砜的合成。
J Org Chem. 2002 Jan 25;67(2):345-56. doi: 10.1021/jo0159183.
9
Synthesis of hydantoins from enantiomerically pure alpha-amino amides without epimerization.
J Org Chem. 2006 Feb 17;71(4):1750-3. doi: 10.1021/jo052474s.
10
Synthesis of Enantiopure α'-Amino α,β-Epoxy Ketones from α'-Amino Bromomethyl Ketones.
J Org Chem. 1999 Jul 9;64(14):5048-5052. doi: 10.1021/jo982435z.
引用本文的文献
1
Tinker, Tailor, Soldier, Spy: The Diverse Roles That Fluorine Can Play within Amino Acid Side Chains.《间谍游戏：氟原子在氨基酸侧链中扮演的多样角色》。
Molecules. 2023 Aug 22;28(17):6192. doi: 10.3390/molecules28176192.
2
The Biophysical Probes 2-fluorohistidine and 4-fluorohistidine: Spectroscopic Signatures and Molecular Properties.2-氟组氨酸和 4-氟组氨酸的生物物理探针：光谱特征和分子性质。
Sci Rep. 2017 Feb 15;7:42651. doi: 10.1038/srep42651.
本文引用的文献
1
Photochemical Schiemann Reaction in Ionic Liquids.离子液体中的光化学席曼反应。
J Fluor Chem. 2007 Jun;128(6):674-678. doi: 10.1016/j.jfluchem.2007.03.012.
2
Biosynthetic incorporation of fluorohistidine into proteins in E. coli: a new probe of macromolecular structure.氟组氨酸在大肠杆菌中生物合成掺入蛋白质：一种大分子结构的新探针。
Chembiochem. 2005 Dec;6(12):2170-3. doi: 10.1002/cbic.200500249.
3
A designed peptide ligase for total synthesis of ribonuclease A with unnatural catalytic residues.一种用于全合成具有非天然催化残基的核糖核酸酶A的设计肽连接酶。
Science. 1994 Oct 14;266(5183):243-7. doi: 10.1126/science.7939659.
4
Photochemical decomposition of diazonium fluoroborates. Application to the synthesis of ring-fluorinated imidazoles.氟硼酸重氮盐的光化学分解。在环氟化咪唑合成中的应用。
J Am Chem Soc. 1971 Jun 16;93(12):3060-1. doi: 10.1021/ja00741a048.
5
Photochemistry of diazonium salts. 3. A new and facile synthesis of 4-fluoroimidazoles.重氮盐的光化学。3. 4-氟咪唑的一种新型简便合成方法。
J Org Chem. 1973 Oct 5;38(20):3647-8. doi: 10.1021/jo00960a053.
6
Photochemistry of diazonium salts. II. Synthesis of 2-fluoro-L-histidine and 2-fluorohistamine, and the halogen lability of 2-fluoroimidazoles.重氮盐的光化学。II. 2-氟-L-组氨酸和2-氟组胺的合成以及2-氟咪唑的卤素不稳定性
J Am Chem Soc. 1973 Dec 12;95(25):8389-92. doi: 10.1021/ja00806a031.
7
Photochemistry of diazonium salts. I. Synthesis of 4-fluoroimidazoles, 4-fluorohistamine, and 4-fluorohistidine.重氮盐的光化学。I. 4-氟咪唑、4-氟组胺和4-氟组氨酸的合成。
J Am Chem Soc. 1973 Jul 11;95(14):4619-24. doi: 10.1021/ja00795a026.
8
Nuclear magnetic resonance and molecular genetic studies of the membrane-bound D-lactate dehydrogenase of Escherichia coli.
Biochemistry. 1987 Jan 27;26(2):549-56. doi: 10.1021/bi00376a029.
9
Active site ligand binding by an inactive ribonuclease S analogue. A quantitative affinity chromatographic study.一种无活性核糖核酸酶S类似物的活性位点配体结合。定量亲和色谱研究。
J Biol Chem. 1977 Oct 25;252(20):6991-4.
Zotero 插件