CAS: 156-56-9; (S)-2-Amino-3-((R)-2-Methylenecyclopropyl)Propanoic Acid

该化合物是天然产生的氨酸衍生物,主要见于果(Bligiah sappida)的种子中,它以毒性而著称,特别是其抑制中链丙酰-CoA脱氢甘蓝酶的能力,这对脂肪酸的新陈代谢至关重要,这种抑制可导致一种被称为牙买加呕吐病的症状,其特点是严重缺血和代谢性干扰.Hypoglycin A是一种无色晶状的固体,在水中可溶解并表现出苦味.它的分子结构包括一个环丙基化合物组,有助于其独特的再活性和生物效应.该化合物被归类为非蛋白性氨基酸,其毒性取决于剂量,因此它必须了解其在食物来源中的存在.由于它潜在的健康风险,因此不能消费不熟食的或含有水果的不熟料.继续研究其毒性和潜在治疗用途的机制,尽管安全仍然是一个首要问题.

结构式图片

欧盟法规

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上下游产品

(2S,4R) α-<(Methylenecyclopropyl)Methyl>Glycine Methyl Ester 144604-83-1

合成工艺路线路线简述

  • 合成目标产物 Hypoglycin 主要起始原料 (S)-(2-Methylenecyclopropyl)Methanol
  • (文献来源)合成步骤主要原料 (S)-(2-Methylenecyclopropyl)Methanol
📜(2S,4Rs)-2-Hydroxy-4-Phenylsulfonyl-5-Trimethylsilyl-1-Pentyl P-Toluenesulfonate置于吡啶,盐酸,Lithium Hydroxide,正丁基锂,四丁基氟化铵,Potassium Carbonate,对甲苯磺酰氯,Lithium Diisopropyl Amide体系中,用 四氢呋喃,甲醇,四氯化碳,乙醚,正己烷,水 用作溶剂,化学反应 121.92H,反应生成(2S)-2-氨基-3-[(1S)-2-亚甲基环丙基]丙酸
参考文献:低血糖素a的各个非对映异构体的不对称全合成.
标题:低血糖素a的各个非对映异构体的不对称全合成.
摘要:利用sharpless环氧化法合成了构成非寻常的含有α-氨基酸次糖苷a的不寻常的亚甲基环丙烷的各个非对映异构体,以允许不对称的亚甲基环丙烷的合成.
Doi:10.1016/s0040-4020(01)89313-3

海关参考信息

专利信息


专利号:US-7452701-B2
优先权日:1998-11-24
标 题:Methods for the preparation of β-amino acids
发明人:FREY PERRY A; RUZICKA FRANK J
权利人:WISCONSIN ALUMNI RES FOUND
摘要:Purified β-amino acids are of considerable interest in the preparation of pharmacologically active compounds and industrial precursors. Although enantiomerically pure β-amino acids can be produced by standard chemical synthesis, this traditional approach is time consuming, requires expensive starting materials, and results in a racemic mixture which must be purified further. However, DNA molecules encoding lysine 2,3-aminomutase can be used to prepare β-amino acids by methods that avoid the pitfalls of chemical synthesis. The present invention provides a method of producing enantiomerically pure β-amino acids from α-amino acids comprising catalyzing the conversion of an α-amino acid to a corresponding β-amino acid by utilizing a lysine 2,3-aminomutase as the catalyst.

专利号:US-2020330400-A1
优先权日:2016-03-16
标 题:Methods for the treatment of cancer using coenzyme q10 and fatty acid metabolism inhibitors
发明人:GESTA STEPHANE; DIERS ANNE R; DADALI-ABEL TULIN
权利人:BERG LLC
摘要:Presented herein are methods for the treatment of oncological disorders by the co-administration of CoQ10 compositions and at least one fatty acid metabolism inhibitor. In one embodiment, the CoQ10 compositions are lipid-containing compositions. The fatty acid metabolism inhibitor may be an inhibitor of fatty acid synthesis, storage, transport or degradation. The fatty acid metabolism inhibitor may also be a modulator of fatty acid structure, for example a fatty acid desaturase or elongase. The fatty acid inhibitor may inhibit any molecule involved in fatty acid metabolism, such as fatty acid synthase (FASN), carnitine palmitoyltransferase 1 (CPT-1), long-chain 3-ketoacyl-CoA thiolase, or stearoyl-CoA desaturase-1 (SCD-1). In embodiments, the fatty acid metabolism inhibitor may be C75, Etomoxir, trimetazidine or A939572.

专利号:US-3880838-A
优先权日:1970-12-16
标 题 :Amino acid derivatives
发明人:BODANSZKY MIKLOS
权利人:SQUIBB & SONS INC
摘要:New lactone intermediates useful in the synthesis of peptides are prepared by reacting an Alpha -amino acid with an active carbonyl compound which forms a Schiff''s base. The latter is treated with a condensing agent so that cyclization occurs and a lactone is formed from which a peptide may be produced by reaction with an amino acid ester and removal of the protecting groups.

专利号:US-3957760-A
优先权日:1970-12-16
标 题:Amino acid derivatives
发明人:BODANSZKY MIKLOS
权利人:SQUIBB & SONS INC
摘要:New lactone intermediates useful in the synthesis of peptides are prepared by reacting an α-amino acid with an active carbonyl compound which forms a Schiff's base. The latter is treated with a condensing agent so that cyclization occurs and a lactone is formed from which a peptide may be produced by reaction with an amino acid ester and removal of the protecting groups.

专利号:US-3704246-A
优先权日:1970-12-16
标 题 :Amino acid derivatives
发明人:BODANSZKY MIKLOS
权利人:SQUIBB & SONS INC
摘要:NEW LACTONE INTERMEDIATES USEFUL IN THE SYNTHESIS OF PEPTIDES ARE PREPARED BY REACTING AN A-AMINO ACID WITH AN ACTIVE CARBONYL COMPOUND WHICH FORMS A SCHIFF''S BASE. THE LATTER IS TREATED WITH A CONDENSING AGENT SO THAT CYCLIZATION OCCURS AND A LACTONE IS FORMED FROM WHICH A PEPTIDE MAY BE PRODUCED BY REACTION WITH AN AMINO ACID ESTER REMOVAL OF THE PROTECTING GROUPS.

供应商参考报价(招募中)

品牌试剂参考报价(招募中)

📌 第三方产品分析报告

✅ COA系统入驻 | 共享模式

主要参考文献

参考标题:Asymmetric Total Synthesis Of The Individual Diastereoisomers Of Hypoglycin A
作者:Jack E. Baldwin,Robert M. Adlington,David Bebbington,Andrew T. Russell
摘要:The Individual Diastereoisomers That Constitute The Unusual Methylenecyclopropane Containing α-Amino Acid Hypoglycin A Have Been Synthesised Utilising The Sharpless Epoxidation To Permit An Asymmetric Methylene Cyclopropane Synthesis.

合成参考文献


摘要:West Indian Medical Journal., 16(193), 1967
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