摩熵化学
数据库官网
小程序
打开微信扫一扫
首页 分子通 化学资讯 化学百科 反应查询 关于我们
请输入关键词

7-甲氧基-L-色氨酸 | 25198-03-2

中文名称
7-甲氧基-L-色氨酸
中文别名
L-7-甲氧基色氨酸
英文名称
L-7-methoxytryptophan
英文别名
7-methoxy-L-tryptophan;(2S)-2-amino-3-(7-methoxy-1H-indol-3-yl)propanoic acid
7-甲氧基-L-色氨酸化学式
CAS
25198-03-2
化学式
C12H14N2O3
mdl
——
分子量
234.255
InChiKey
MUZROTSTMQSBFK-VIFPVBQESA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    -1.1
  • 重原子数:
    17
  • 可旋转键数:
    4
  • 环数:
    2.0
  • sp3杂化的碳原子比例:
    0.25
  • 拓扑面积:
    88.3
  • 氢给体数:
    3
  • 氢受体数:
    4

反应信息

  • 作为反应物:
    描述:
    3-甲基丁-2-烯基膦酰磷酸氢酯7-甲氧基-L-色氨酸甘油2-巯基乙醇 作用下, 反应 0.17h, 生成 7-methoxy-4-(dimethylallyl)tryptophan
    参考文献:
    名称:
    Dimethylallyltryptophan synthase. An enzyme-catalyzed electrophilic aromatic substitution
    摘要:
    Dimethylallyltryptophan (DMAT) synthase catalyzes the alkylation of L-tryptophan at C(4) by dimethylallyl diphosphate (DMAPP) in the first pathway-specific step in the biosynthesis of ergot alkaloids. The mechanism of the reaction was studied with analogs of both substrates. Five 7-substituted derivatives of N-acetyltryptophan (2, Z = OCH3, CH3, F, CF3, and NO2) were synthesized. The L enantiomers of the free amino acids were obtained by selective hydrolysis of the racemate using aminoacylase from Aspergillus. In addition, the E and Z fluoromethyl and difluoromethyl analogs of DMAPP (1, Y = CH3, CH2F, CHF2) were prepared. Rates of the enzyme-catalyzed reactions were measured for the dimethylallyl derivatives with L-tryptophan and for the L-tryptophan derivatives with DMAPP. In addition, the relative reactivities of the methanesulfonate derivatives of the DMAPP analogs were determined for solvolysis in aqueous acetone. A Hammett plot for the tryptophan analogs gave a good linear correlation with rho = -2.0. In addition, a Hammett plot of the logarithms of the relative rates of solvolysis and enzyme-catalyzed alkylation gave a positive linear correlation. These results indicate that the prenyl-transfer reaction catalyzed by DMAT synthase is an electrophilic aromatic substitution and is mechanistically similar to the electrophilic alkylation catalyzed by farnesyl diphosphate synthase.
    DOI:
    10.1021/ja00045a004
  • 作为产物:
    描述:
    参考文献:
    名称:
    ( - ) - 12甲氧基12-甲氧基取代的Sarpagine吲哚生物碱包括的合成一般方法Ñ b -methylvoachalotine,(+) - 12甲氧基Ñ一个-methylvellosimine,(+) - 12-Methoxyaffinisine,和(-)-紫红色的茶碱
    摘要:
    的对映体特异性合成7-甲氧基d -色氨酸乙酯通过用一个基于Schöllkopf-手性辅助良好产率的杂环化拉洛克过程的组合完成。然后将该酯在第一区域专一采用,(+)立体有择的全合成- 12甲氧基Ñ一个-methylvellosimine,(+) - 12-methoxyaffinisine,( - ) - fuchsiaefoline和12甲氧基Ñ b -methylvoachalotine具有极好的总产量。非对称的Pictet-Spengler反应和烯醇盐驱动的钯催化的交叉偶联过程是关键步骤。通过(+)-12-甲氧基-N之间的Tollens反应建立12-甲氧基-N b-甲基voachalotine的C(16)的季中心一个-methylvellosimine和甲醛以形成二醇17。在二醇两个前手性伯醇17是由羟基的氧化环化(DDQ)在轴向位置分化17与在苄基现在的位置是[C(6)],以形成环状醚[C(6)-O
    DOI:
    10.1021/jo052081t
点击查看最新优质反应信息

文献信息

  • Inhibitors of cellular necrosis
    申请人:Cuny D. Gregory
    公开号:US20050119260A1
    公开(公告)日:2005-06-02
    The present invention relates to compounds and pharmaceutical preparations and their use in therapy for preventing or treating trauma, ischemia, stroke and degenerative diseases associated with cell death. Methods and compositions of the invention are particularly useful for treating neurological disorders associated with cellular necrosis.
    本发明涉及化合物、药物制剂及其在预防或治疗与细胞死亡相关的创伤、缺血、中风和退行性疾病中的应用的治疗。本发明的方法和组合物特别适用于治疗与细胞坏死相关的神经系统疾病。
  • [EN] HIGHLY ACTIVE SELF-SUFFICIENT NITRATION BIOCATALYSTS<br/>[FR] BIOCATALYSEURS DE NITRATION AUTO-SUFFISANTS HAUTEMENT ACTIFS
    申请人:UNIV FLORIDA
    公开号:WO2018081456A1
    公开(公告)日:2018-05-03
    The disclosure relates to the field of fusion proteins. In some aspects, the disclosure relates to artificial fusion proteins comprising cytochrome P450 enzymes linked to reductase enzymes and uses thereof. In some aspects, the disclosure relates to compounds produced by artificial cytochrome P450 enzymes.
    该披露涉及融合蛋白的领域。在某些方面,该披露涉及人工融合蛋白,其中包括与还原酶酶相连的细胞色素P450酶,并其用途。在某些方面,该披露涉及由人工细胞色素P450酶产生的化合物。
  • INHIBITORS OF CELLULAR NECROSIS
    申请人:Cuny Gregory D.
    公开号:US20120149702A1
    公开(公告)日:2012-06-14
    The present invention relates to compounds and pharmaceutical preparations and their use in therapy for preventing or treating trauma, ischemia, stroke and degenerative diseases associated with cell death. Methods and compositions of the invention are particularly useful for treating neurological disorders associated with cellular necrosis.
    本发明涉及化合物和药物制剂及其在预防或治疗与细胞死亡相关的创伤、缺血、中风和退行性疾病中的应用。本发明的方法和组合物特别适用于治疗与细胞坏死相关的神经系统疾病。
  • Novel anti-infective compound
    申请人:Eberhard Karls Universität Tübingen
    公开号:EP3072899A1
    公开(公告)日:2016-09-28
    The invention relates to novel infective agents, the use thereof for the production of a pharmaceutical composition for the treatment and prophylaxes of a disease, preferably an infectious disease, a pharmaceutical composition comprising said compound, and to methods of producing said compounds.
    本发明涉及新型感染性制剂、利用其生产治疗和预防疾病(最好是传染病)的药物组合物、包含所述化合物的药物组合物以及生产所述化合物的方法。
  • Artificial self-sufficient cytochrome P450s
    申请人:University of Florida Research Foundation, Incorporated
    公开号:US10550079B2
    公开(公告)日:2020-02-04
    The disclosure relates to the field of fusion proteins. In some aspects, the invention to artificial fusion proteins comprising cytochrome P450 enzymes linked to reductase enzymes and uses thereof. In some aspects, the disclosures relates to compounds produced by artificial cytochrome P450 enzymes.
    本发明涉及融合蛋白领域。在某些方面,本发明涉及由与还原酶连接的细胞色素 P450 酶组成的人工融合蛋白及其用途。在某些方面,本发明涉及由人工细胞色素 P450 酶产生的化合物。
查看更多

同类化合物

(Z)-3-[[[2,4-二甲基-3-(乙氧羰基)吡咯-5-基]亚甲基]吲哚-2--2- (S)-(-)-5'-苄氧基苯基卡维地洛 (R)-(+)-5'-苄氧基卡维地洛 (R)-卡洛芬 (N-(Boc)-2-吲哚基)二甲基硅烷醇钠 (E)-2-氰基-3-(5-(2-辛基-7-(4-(对甲苯基)-1,2,3,3a,4,8b-六氢环戊[b]吲哚-7-基)-2H-苯并[d][1,2,3]三唑-4-基)噻吩-2-基)丙烯酸 (4aS,9bR)-6-溴-2,3,4,4a,5,9b-六氢-1H-吡啶并[4,3-B]吲哚 (3Z)-3-(1H-咪唑-5-基亚甲基)-5-甲氧基-1H-吲哚-2-酮 (3Z)-3-[[[4-(二甲基氨基)苯基]亚甲基]-1H-吲哚-2-酮 (3R)-(-)-3-(1-甲基吲哚-3-基)丁酸甲酯 (3-氯-4,5-二氢-1,2-恶唑-5-基)(1,3-二氧代-1,3-二氢-2H-异吲哚-2-基)乙酸 齐多美辛 鸭脚树叶碱 鸭脚木碱,鸡骨常山碱 鲜麦得新糖 高氯酸1,1’-二(十六烷基)-3,3,3’,3’-四甲基吲哚碳菁 马鲁司特 马鞭草(VERBENAOFFICINALIS)提取物 马来酸阿洛司琼 马来酸替加色罗 顺式-ent-他达拉非 顺式-1,3,4,4a,5,9b-六氢-2H-吡啶并[4,3-b]吲哚-2-甲酸乙酯 顺式-(+-)-3,4-二氢-8-氯-4'-甲基-4-(甲基氨基)-螺(苯并(cd)吲哚-5(1H),2'(5'H)-呋喃)-5'-酮 靛青二磺酸二钾盐 靛藍四磺酸 靛红联二甲酚 靛红磺酸钠 靛红磺酸 靛红乙烯硫代缩酮 靛红-7-甲酸甲酯 靛红-5-磺酸钠 靛红-5-磺酸 靛红-5-硫酸钠盐二水 靛红-5-甲酸甲酯 靛红 靛玉红衍生物E804 靛玉红3'-单肟5-磺酸 靛玉红-3'-单肟 靛玉红 靛噻 青色素3联己酸染料,钾盐 雷马曲班 雷莫司琼杂质13 雷莫司琼杂质12 雷莫司琼杂质 雷替尼卜定 雄甾-1,4-二烯-3,17-二酮 阿霉素的代谢产物盐酸盐 阿贝卡尔 阿西美辛杂质3