trans-3,4-epoxy-L-proline | 159551-86-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: trans-3,4-epoxy-L-proline
• 英文别名: (2S,3R,4S)-3,4-epoxyproline；6-Oxa-3-azabicyclo[3.1.0]hexane-2-carboxylic acid, (1R,2S,5S)-；(1R,2S,5S)-6-oxa-3-azabicyclo[3.1.0]hexane-2-carboxylic acid
• CAS: 159551-86-7
• 化学式: C₅H₇NO₃
• 分子量: 129.115
• InChiKey: XCPHRJMOUIKQLM-HZLVTQRSSA-N

物化性质

• 沸点：
  325.1±37.0 °C(Predicted)
• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  61.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2s,4r)-1,2-二苄氧羰基-4-羟基吡咯烷 在 palladium on activated charcoal 吡啶 、 N-甲基咪唑 、 sodium tetrahydroborate 、 2,2'-Dimethyl-5,5'-di-tert-butyl-4,4'-dihydroxy-diphenyl-sulfid, Lanotox 、 氢气 、 双氧水 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 叔丁醇 为溶剂， 30.0 ℃ 、101.33 kPa 条件下， 反应 7.0h， 生成 trans-3,4-epoxy-L-proline
  参考文献：
  名称：

  （2 S，3 R，4 S），（2 S，3 S，4 R）-环氧脯氨酸和氨基羟脯氨酸的合成

  摘要：

  2小号，3 - [R，4小号-和2小号，3小号，4 - [R -环氧大号-prolines从合成反式-4-羟基-大号脯氨酸。环氧脯氨酸的立体化学构型的分配是通过nOe研究和化学相关性实现的。通过用NaN 3开环，然后脱保护得到氨基羟脯氨酸，简要地研究了被保护的环氧化物的合成效用。

  DOI：

  10.1016/s0040-4020(97)10352-0

文献信息

• Epoxide derivatives of pipecolic acid and proline are inhibitors of pipecolate oxidase
  作者：Bin Ho、T.Mark Zabriskie

  DOI：10.1016/s0960-894x(98)00106-1

  日期：1998.4

  The cis-4,5-epoxide derivative of L-pipecolic acid (2S,4S,5R-epoxypipecolic acid, cis-3) was synthesized and found to serve as an excellent substrate for L-pipecolate oxidase (L-PO) and also to cause time-dependent, irreversible inactivation of the enzyme. Data are presented showing this compound is a mechanism-based inhibitor of L-PO, whereas 2S,3R,4S-epoxyproline acts as a reversible inhibitor.

  合成了L-哌酸的顺式4,5-环氧衍生物（2S，4S，5R-环氧哌酸，cis-3），发现其可作为L-哌酸氧化酶（L-PO）的极佳底物导致时间依赖性，不可逆的酶失活。提供的数据表明该化合物是基于机理的L-PO抑制剂，而2S，3R，4S-环氧脯氨酸起可逆抑制剂的作用。
• Synthesis of and from S-pyroglutamic acid. Regio- and diastereoselective ring opening of its derivatives
  作者：Claus Herdeis、Andrea Aschenbrenner、Armin Kirfel、Franz Schwabenländer

  DOI：10.1016/s0957-4166(97)00261-9

  日期：1997.7

  The pyroglutamic acid derivative 4 was converted through several steps into 2S,3R,4S-epoxyproline 8. Key steps of the reaction sequence were the stereoselective epoxidation of 4 to 5 and the chemoselective reduction of the amide group of 5 with concomitant transformation of the acetal moiety into the N-benzyl protecting group without oxirane ring opening. The air sensitive benzyl derivative was transformed

  通过几个步骤将焦谷氨酸衍生物4转化为2 S，3 R，4 S-环氧脯氨酸8。反应顺序的关键步骤是的立体选择性环氧化4至5和化学选择性还原的酰胺基的5与缩醛部分的伴随转变成N-苄基保护基，而不环氧乙烷开环。将对空气敏感的苄基衍生物转化为稳定的N-Boc脯氨醇衍生物6。氧化6得到被保护的环氧脯氨酸衍生物7。解除保护7配备了对映体2 S，3 R，4 S-环氧脯氨酸8。环氧乙烷6或16的开环是在完全区域控制下用C，N，Cl亲核试剂完成的。叠氮基脯氨醇9用作合成Epiminoproline衍生物23的起始材料。
• Substrate selectivities of proline hydroxylases
  作者：Takeshi Shibasaki、Wataru Sakurai、Atsuhiro Hasegawa、Youichi Uosaki、Hideo Mori、Mayumi Yoshida、Akio Ozaki

  DOI：10.1016/s0040-4039(99)00944-2

  日期：1999.7

  Substrate selectivities of microbial proline 4-hydroxylase and proline 3-hydroxylases, all of which were purified from recombinant Escherichia coli, were investigated. L-2-Azetidine carboxylate, 3,4-dehydro-L-proline and L-pipecolinic acid were hydroxylated by those enzymes in regio- and stereospecific manner. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Substrate specificity of proline-4-hydroxylase: Chemical and enzymatic synthesis of 2S,3R,4S-epoxyproline
  作者：Jack E. Baldwin、Robert A. Field、Christopher C. Lawrence、Victor Lee、J.Kenneth Robinson、Christopher J. Schofield

  DOI：10.1016/s0040-4039(00)60753-0

  日期：1994.6

  The substrate specificity of L-proline 4-hydroxylase, a 2-oxoglutarate dependent dioxygenase from Streptomyces griseoviridus P8648, was investigated. Preliminary assays measuring turnover of 2-oxoglutarate indicated 3,4-dehydro-L-proline was an efficient substrate. The identity of the product was shown to be 2S,3R,4S-epoxy-L-proline by comparison with synthetic 2S,3R,4S- and 2S,3S,4R-epoxy-L-prolines.
• Synthesis of (2S, 3R, 4S), (2S, 3S, 4R)-epoxyprolines and aminohydroxyprolines
  作者：J. Kenneth Robinson、Victor Lee、Timothy D.W. Claridge、Jack E. Baldwin、Christopher J. Schofield

  DOI：10.1016/s0040-4020(97)10352-0

  日期：1998.1

  2S, 3R, 4S- and 2S, 3S, 4R-epoxy-L-prolines were synthesised from trans-4-hydroxy-L-proline. Assignment of the stereochemical configurations of the epoxy prolines was achieved by n.O.e. studies and chemical correlation. The synthetic utility of the protected epoxides was investigated briefly by ring opening with NaN3, followed by deprotection to give aminohydroxy prolines.

  2小号，3 - [R，4小号-和2小号，3小号，4 - [R -环氧大号-prolines从合成反式-4-羟基-大号脯氨酸。环氧脯氨酸的立体化学构型的分配是通过nOe研究和化学相关性实现的。通过用NaN 3开环，然后脱保护得到氨基羟脯氨酸，简要地研究了被保护的环氧化物的合成效用。

表征谱图