5-溴色氨酸 | 93299-40-2

• 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
• 中文名称: 5-溴色氨酸
• 中文别名: 5-溴-D-色氨酸；D-5-溴色氨酸；2-氯-4-氟苯甲基氯
• 英文名称: 5-bromo-D-tryptophan
• 英文别名: (R)-2-amino-3-(5-bromo-1H-indol-3-yl)propanoic acid；(R)-5-bromotryptophan；(2R)-2-ammonio-3-(5-bromo-1H-indol-3-yl)propanoate；(2R)-2-azaniumyl-3-(5-bromo-1H-indol-3-yl)propanoate
• CAS: 93299-40-2
• 化学式: C₁₁H₁₁BrN₂O₂
• 分子量: 283.125
• InChiKey: KZDNJQUJBMDHJW-SECBINFHSA-N

物化性质

• 沸点：
  495.8±45.0 °C(Predicted)
• 密度：
  1.704±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.1
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5-溴-DL-色氨酸	5-bromo-DL-tryptophan	6548-09-0	C11H11BrN2O2	283.125
  ——	Nα-acetyl-5-bromo-D-tryptophan	75816-16-9	C13H13BrN2O3	325.162

反应信息

• 作为反应物：
  描述：

  5-溴色氨酸 在 三乙基硅烷 、 氯化亚砜 、 N-羟基-7-氮杂苯并三氮唑 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 85.17h， 生成 methyl (5S,9S,12R)-12-((5-bromo-1H-indol-3-yl)methyl)-9-((tert-butyldiphenylsilyl)oxy)-1-(9H-fluoren-9-yl)-3,6,10-trioxo-5-(2-oxo-2-(tritylamino)ethyl)-2-oxa-4,7,11-triazatridecan-13-oate
  参考文献：
  名称：

  Application of the DP4 Probability Method to Flexible Cyclic Peptides with Multiple Independent Stereocenters: The True Structure of Cyclocinamide A

  摘要：

  A DP4 protocol has been successfully utilized to establish the true structure of the natural product cyclocinamide A, a flexible cyclic peptide with four isolated stereocenters. Benchmarking the necessary level of theory required to successfully predict the NMR spectra of three previously synthesized isomers of cyclocinamide A led to the prediction of the natural stereochemistry as 4S, 7R, 11R, 14S, which has been confirmed by total synthesis.

  DOI：

  10.1021/acs.orglett.8b01756
• 作为产物：
  描述：

  5-溴-DL-色氨酸 在 IvoA acetyltransferase 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 以 aq. phosphate buffer 为溶剂， 反应 12.0h， 以99%的产率得到
  参考文献：
  名称：

  Complete Stereoinversion of l-Tryptophan by a Fungal Single-Module Nonribosomal Peptide Synthetase

  摘要：

  Single-module nonribosomal peptide synthetases (NRPSs) and NRPS-like enzymes activate and transform carboxylic acids in both primary and secondary metabolism and are of great interest due to their biocatalytic potentials. The single-module NRPS IvoA is essential for fungal pigment biosynthesis. Here, we show that IvoA catalyzes ATP-dependent unidirectional stereo inversion of L-tryptophan to D-tryptophan with complete conversion. While the stereoinversion is catalyzed by the epimerization (E) domain, the terminal condensation (C) domain stereoselectively hydrolyzes D-tryptophanyl-S-phosphopantetheine thioester and thus represents a noncanonical C domain function. Using IvoA, we demonstrate a biocatalytic stereoinversion/deracemization route to access a variety of substituted D-tryptophan analogs in high enantiomeric excess.

  DOI：

  10.1021/jacs.9b08898

文献信息

• COMPOUNDS AND METHOD OF USE
  申请人：Ferro Therapeutics, Inc.

  公开号：US20190263802A1

  公开（公告）日：2019-08-29

  This present disclosure relates to compounds with ferroptosis inducing activity, a method of treating a subject with cancer with the compounds, and combination treatments with a second therapeutic agent.

  本公开涉及具有诱导铁死亡活性的化合物，一种使用这些化合物治疗癌症患者的方法，以及与第二种治疗药物的联合治疗。
• PROCESS FOR PREPARING VAPREOTIDE
  申请人：Palle Acharyulu Venkata Raghavendra

  公开号：US20070111930A1

  公开（公告）日：2007-05-17

  A solution phase process for preparing vapreotide, having the formula:

  制备vapreotide的溶液相过程，其化学式为：
• General synthesis of unnatural 4-, 5-, 6-, and 7-bromo-d-tryptophans by means of a regioselective indole alkylation
  作者：Francesca Bartoccini、Fabiola Fanini、Michele Retini、Giovanni Piersanti

  DOI：10.1016/j.tetlet.2020.151923

  日期：2020.5

  A general two-step approach to enantiopure bromotryptophans from unprotected bromoindoles has been developed. Indole nucleophiles prepared with MeMgCl in the presence of CuCl reacted with cyclic sulfamidates derived from enantiopure d-serine to form 4-, 5-, 6-, or 7-bromo-d-tryptophan and some other halogenated tryptophans in moderate yields but with complete regioselectivity. The bromotryptophan derivatives

  已经开发了从未保护的溴吲哚中对映体纯的溴色氨酸的一般两步方法。与格氏引发剂在CuCl的存在下制备的吲哚的亲核试剂与对映体纯衍生环状sulfamidates反应d -丝氨酸以形成4-，5-，6-或7-溴d色氨酸，并且在中等产率，但是与完全一些其它卤代色氨酸区域选择性。溴色氨酸衍生物在温和条件下脱保护。
• Biologically active lysine containing octapeptides
  申请人：The Administrators of The Tulane University Educational Fund

  公开号：EP0203031A2

  公开（公告）日：1986-11-26

  Novel compositions of the formula wherein A represents an L, D or DL amino-acid selected from the group consisting of Ala, Val, Phe, p-CI-Phe, Trp, Pro, Ser, Thr, Glu, Gly, Beta Ala, Abu, N-Me Ala, 5-F-Trp, 5-Br-Trp, 5-Cl-Trp, their acetylated derivatives or a pharmaceutically acceptable acid addition salt thereof; B represents an L, D or DL amino acid amide selected from the group consisting of Thr NH2, Val NH,, Pro NH2, HO-Pro NH2, Ser NH2, Tyr NH2, Trp NH2, 5-F-Trp NH,, For-Trp NH., Ala NH2, Gly NH2, Me Ala NH2; X represents L-Phe or L-Tyr, Y represents L-Thr or L-Val; Z is L, D or DL-5-F-Trp, 5-Br-Trp, 5-C1-Trp, 5-I-Trp or D-Trp; and C" and C' represent L or D Cys, Abu, Asp or Lys; provided that where C' is Cys, C" is also Cys and where C' or C" are other than Cys, C" is different from C' and is other than Cys and the pharmaceutically acceptable acid addition salts thereof; are useful as agents for inhibiting the release of growth hormone, for the treatment of gastrointestinal disorders and for therapy of certain cancers and the management of diabetes. These biologically active octapeptides all possess a terminal amino acid amide at position 8 and are prepared by solid phase methods.

  式中的新型组合物 式中 A 代表选自以下组别的 L、D 或 DL 氨基酸：Ala、Val、Phe、p-CI-Phe、Trp、Pro、Ser、Thr、Glu、Gly、Beta Ala、Abu、N-Me Ala、5-F-Trp、5-Br-Trp、5-Cl-Trp、它们的乙酰化衍生物或其药学上可接受的酸加成盐； B 代表选自 Thr NH2、Val NH、Pro NH2、HO-Pro NH2、Ser NH2、Tyr NH2、Trp NH2、5-F-Trp NH、For-Trp NH、Ala NH2、Gly NH2、Me Ala NH2 所组成的组的 L、D 或 DL 氨基酸酰胺； X 代表 L-Phe或 L-Tyr、 Y 代表 L-Thr 或 L-Val Z 是 L、D 或 DL-5-F-Trp、5-Br-Trp、5-C1-Trp、5-I-Trp 或 D-Trp；以及 C "和 C'代表 L 或 D Cys、Abu、Asp 或 Lys；条件是当 C' 是 Cys 时，C "也是 Cys，当 C' 或 C "不是 Cys 时，C "不同于 C'，也不是 Cys 及其药学上可接受的酸加成盐；可用作抑制生长激素释放、治疗胃肠道疾病、治疗某些癌症和糖尿病的药物。这些具有生物活性的八肽都在第 8 位具有一个末端氨基酸酰胺，并通过固相方法制备。
• Allen, Mark C.; Brundish, Derek E.; Fullerton, Joseph D., Journal of the Chemical Society. Perkin transactions I, 1986, p. 989 - 1004
  作者：Allen, Mark C.、Brundish, Derek E.、Fullerton, Joseph D.、Wade, Roy

  DOI：——

  日期：——