(3S)-3-hydroxyoxytryptophan | 76604-82-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (3S)-3-hydroxyoxytryptophan
• 英文别名: dioxindolyl-L-alanine；3-[(3S)-3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl]-L-alanine；(2S)-2-amino-3-[(3S)-3-hydroxy-2-oxo-1H-indol-3-yl]propanoic acid
• CAS: 76604-82-5
• 化学式: C₁₁H₁₂N₂O₄
• 分子量: 236.227
• InChiKey: BZRCOYDQHJWPQZ-CPCISQLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S)-3-hydroxyoxytryptophan 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 32.0h， 生成 N-phthaloyldioxindolyl-L-alanine spirolactone
  参考文献：
  名称：

  Preparative separation of the diastereoisomers of dioxindolyl-L-alanine and assignment of stereochemistry at C-3

  摘要：

  DOI：

  10.1021/jo00303a027
• 作为产物：
  描述：

  β-Dioxindolyl-DL-alanin 生成 (3S)-3-hydroxyoxytryptophan
  参考文献：
  名称：

  Preparative separation of the diastereoisomers of dioxindolyl-L-alanine and assignment of stereochemistry at C-3

  摘要：

  DOI：

  10.1021/jo00303a027

文献信息

• The Halicylindramides, Farnesoid X Receptor Antagonizing Depsipeptides from a <i>Petrosia</i> sp. Marine Sponge Collected in Korea
  作者：Dongyup Hahn、Hiyoung Kim、Inho Yang、Jungwook Chin、Hoosang Hwang、Dong Hwan Won、Byoungchan Lee、Sang-Jip Nam、Merrick Ekins、Hyukjae Choi、Heonjoong Kang

  DOI：10.1021/acs.jnatprod.5b00871

  日期：2016.3.25

  Three new structurally related depsipeptides, halicylindramides F–H (1–3), and two known halicylindramides were isolated from a Petrosia sp. marine sponge collected off the shore of Youngdeok-Gun, East Sea, Republic of Korea. Their planar structures were elucidated by extensive spectroscopic data analyses including 1D and 2D NMR data as well as MS data. The absolute configurations of halicylindramides

  三个新的结构上相关的缩酚酸肽，halicylindramides F-H（1 - 3），以及两个公知的halicylindramides从一个分离Petrosia藻。海洋海绵收集在大韩民国东海Youngdeok-Gun的海岸上。通过广泛的光谱数据分析（包括1D和2D NMR数据以及MS数据）阐明了它们的平面结构。halicylindramides F-H（的绝对构型1 - 3）通过的Marfey可在配有Edman降解组合方法测定。卤代吲哚酰胺G（2）和H（3）的二氧吲哚丙氨酸（Dioia）残基在C-4的绝对构型确定为4 S和4。R分别基于ECD光谱。Dioia在C-2配置2和3被推测都为2 - [R基于所述halicylindramides的共享生物合成。Halicylindramides F（1），A（4）和C（5）显示人类法呢类X受体（hFXR）拮抗活性，但不直接与hFXR结合。
• IDO Inhibitors
  申请人：Mautino Mario

  公开号：US20110053941A1

  公开（公告）日：2011-03-03

  Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

  目前提供以下方法：(a) 通过接触本文中描述的化合物的调节有效量与吲哚胺2,3-二氧化酶相互作用，从而调节吲哚胺2,3-二氧化酶的活性；(b) 治疗需要吲哚胺2,3-二氧化酶(IDO)介导的免疫抑制的患者，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(c) 治疗需要抑制吲哚胺-2,3-二氧化酶酶活性的医疗状况，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(d) 增强抗癌治疗的有效性，包括给予抗癌剂和本文中描述的化合物；(e) 治疗与癌症相关的肿瘤特异性免疫抑制，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(f) 治疗与传染病相关的免疫抑制，例如HIV-1感染，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量。
• Enzymatic Synthesis of Noncanonical α‐Amino Acids Containing γ‐Tertiary Alcohols
  作者：Rui Zhang、Chenghua Zhang、Jiamu Tan、Yifan He、Dan Zhuo、Jingxuan Zhang、Zhenzhen Luo、Qiaoqiao Li、Jiaying Yao、Changqiang Ke、Chunping Tang、Yang Ye、Shijun He、Xiang Sheng、Cangsong Liao

  DOI：10.1002/anie.202318550

  日期：2024.2.12

  An enzymatic decarboxylative aldol reaction was developed for the synthesis of noncanonical α-amino acids containing γ-tertiary alcohol groups. The modularity of the electrophile enabled access to four classes of ncAAs with high efficiency as well as excellent regioselectivity and stereoselectivity.

  开发了一种酶促脱羧羟醛反应，用于合成含有 γ-叔醇基团的非常规 α-氨基酸。亲电子试剂的模块化使得能够以高效率以及优异的区域选择性和立体选择性获得四类 ncAA。
• LABROO, RITA B.;COHEN, LOUIS A., J. ORG. CHEM., 55,(1990) N6, C. 4901-4904
  作者：LABROO, RITA B.、COHEN, LOUIS A.

  DOI：——

  日期：——
• Preparative separation of the diastereoisomers of dioxindolyl-L-alanine and assignment of stereochemistry at C-3
  作者：Rita B. Labroo、Louis A. Cohen

  DOI：10.1021/jo00303a027

  日期：1990.8