N-boc-1-甲基-L-色氨酸 | 109927-44-8

• 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: N-boc-1-甲基-L-色氨酸
• 英文名称: N^α-(tert-butoxycarbonyl)-1-methyl-L-tryptophan
• 英文别名: (S)-2-((tert-Butoxycarbonyl)amino)-3-(1-methyl-1H-indol-3-yl)propanoic acid；(2S)-3-(1-methylindol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 109927-44-8
• 化学式: C₁₇H₂₂N₂O₄
• mdl: MFCD28987645
• 分子量: 318.373
• InChiKey: OHPBREBKPBFZCY-ZDUSSCGKSA-N

物化性质

• 熔点：
  140-142 °C
• 沸点：
  525.3±45.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 储存条件：
  | 2-8°C |

反应信息

• 作为反应物：
  描述：

  N-boc-1-甲基-L-色氨酸 在 盐酸 、 N,N'-羰基二咪唑 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Matrix Metalloproteinase Inhibitors:  A Structure−Activity Study

  摘要：

  Modifications around the dipeptide-mimetic core of a hydroxamic acid based matrix metalloproteinase inhibitor were studied. These variations incorporated a variety of natural, unnatural, and synthetic amino acids in addition to modifications of the P1' and P3' substituents. The results of this study indicate the following structural requirements: (1) Two key hydrogen bonds must be present between the enzyme and potent substrates. (2) Potent inhibitors must possess strong zinc-binding functionalities. (3) The potential importance of the hydrophobic group at position R3 as illustrated by its ability to impart greater relative potency against stromelysin when larger hydrophobic groups are used. (4) Requirements surrounding the nature of the amino acid appear to be more restrictive for stromelysin than for neutrophil collagenase, 72 kDa gelatinase, and 92 kDa gelatinase. These requirements may involve planar fused-ring aryl systems and possibly hydrogen-bonding capabilities.

  DOI：

  10.1021/jm970494j
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 三乙胺 、 potassium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 24.08h， 生成 N-boc-1-甲基-L-色氨酸
  参考文献：
  名称：

  使用草酰氯对 N-叔丁氧羰基 (N-Boc) 基团进行温和脱保护

  摘要：

  我们报告了一种温和的方法，通过在甲醇中使用草酰氯，从结构多样的一组化合物（包括脂肪族、芳香族和杂环底物）中选择性脱保护N -Boc 基团。反应在室温条件下进行 1-4 小时，产率高达 90%。这种温和的程序应用于一种混合的药用活性化合物 FC1，它是一种新型的 IDO1 和 DNA Pol γ 双重抑制剂。对于这种去保护策略，假设了涉及草酰氯的亲电特性的更广泛的机制。

  DOI：

  10.1039/d0ra04110f

文献信息

• Sap6, a secreted aspartyl proteinase, participates in maintenance the cell surface integrity of Candida albicans
  作者：Leh-Miauh Buu、Yee-Chun Chen

  DOI：10.1186/1423-0127-20-101

  日期：2013.12

  The polymorphic species Candida albicans is the major cause of candidiasis in humans. The secreted aspartyl proteinases (Saps) of C. albicans, encoded by a family of 10 SAP genes, have been investigated as the virulent factors during candidiasis. However, the biological functions of most Sap proteins are still uncertain. In this study, we applied co-culture system of C. albicans and THP-1 human monocytes to explore the pathogenic roles and biological functions of Sap proteinases. After 1 hr of co-culture of C. albicans strains and THP-1 human monocytes at 37°C, more than 60% of the THP-1-engulfed wild type and Δsap5 Candida cells were developing long hyphae. However, about 50% of THP-1-engulfed Δsap6 Candida cells were generating short hyphae, and more dead Candida cells were found in Δsap6 strain that was ingested by THP-1 cells (about 15% in Δsap6 strain vs. 2 ~ 2.5% in SC5314 and Δsap5 strains). The immunofluorescence staining demonstrated that the Sap6 is the major hyphal tip located Sap protein under THP-1 phagocytosis. The sap6-deleted strains (Δsap6, Δsap4/6, and Δsap5/6) appeared slower growth on Congo red containing solid medium at 25°C, and the growth defect was exacerbated when cultured at 37°C in Congo red or SDS containing medium. In addition, more proteins were secreted from Δsap6 strain and the β-mercaptoethanol (β-ME) extractable surface proteins from Δsap6 mutant were more abundant than that of extracted from wild type strain, which included the plasma membrane protein (Pma1p), the ER-chaperone protein (Kar2p), the protein transport-related protein (Arf1p), the cytoskeleton protein (Act1), and the mitochondrial outer membrane protein (porin 1). Moreover, the cell surface accessibility was increased in sap6-deleted strains. From these results, we speculated that the cell surface constitution of C. albicans Δsap6 strain was defect. This may cause the more accessible of β-ME to disulfide-bridged cell surface components and may weaken the resistance of Δsap6 strain encountering phagocytosis of THP-1 cells. Sap6 protein displays a significant function involving in maintenance the cell surface integrity.

  多形性物种白色念珠菌是人念珠菌病的主要病因。白色念珠菌分泌的天冬氨酸蛋白酶(SAPs)由一组10个SAP基因编码,已被研究作为念珠菌病的毒力因子。然而,大多数SAP蛋白的生物学功能仍然不确定。在本研究中,我们采用了白色念珠菌和THP-1人单核细胞的共培养系统来探索SAP蛋白酶的致病作用和生物学功能。在37°C下共培养白色念珠菌株和THP-1人单核细胞1小时后,超过60%的THP-1吞噬的野生型和ΔSAP5白色念珠菌细胞正在发育长菌丝。然而,大约50%的THP-1吞噬的ΔSAP6白色念珠菌细胞正在产生短菌丝,并且在被THP-1细胞吞噬的ΔSAP6菌株中发现了更多的死白色念珠菌细胞(ΔSAP6菌株中约15%,而SC5314和ΔSAP5菌株中约2~2.5%)。免疫荧光染色证明,SAP6是THP-1吞噬作用下位于菌丝顶端的主要SAP蛋白。SAP6缺失菌株(ΔSAP6,ΔSAP4/6和ΔSAP5/6)在含有刚果红的固体培养基上在25°C下生长较慢,并且在含有刚果红或SDS的培养基中在37°C下培养时生长缺陷加剧。此外,从ΔSAP6菌株分泌的蛋白更多,并且从ΔSAP6突变体提取的可溶于β-巯基乙醇(β-ME)的表面蛋白比从野生型菌株提取的更丰富,其中包括质膜蛋白(Pma1p)、内质网伴侣蛋白(Kar2p)、蛋白质运输相关蛋白(Arf1p)、细胞骨架蛋白(Act1)和线粒体外膜蛋白(孔蛋白1)。此外,SAP6缺失菌株的细胞表面可及性增加。从这些结果中,我们推测ΔSAP6白色念珠菌菌株的细胞表层结构存在缺陷。这可能导致β-ME更容易接近二硫键连接的细胞表面成分,并且可能削弱ΔSAP6菌株在遇到THP-1细胞的吞噬作用时的抵抗力。SAP6蛋白在维持细胞表面完整性方面显示出重要的作用。
• Dendritic Biomimicry: Microenvironmental Hydrogen-Bonding Effects on Tryptophan Fluorescence
  作者：Stéphanie Koenig、Lars Müller、David K. Smith

  DOI：10.1002/1521-3765(20010302)7:5<979::aid-chem979>3.0.co;2-c

  日期：2001.3.2

  a range of different solvents. This paper presents the syntheses of these novel dendritic structures and discusses their emission spectra in terms of both solvent and dendritic effects. In the first series of dendrimers, the NH group of the indole ring is available for hydrogen bonding, whilst in the second series, the indole NH group has been converted to NMe. Direct comparison of the emission wavelengths

  已经合成了两个系列的经树状修饰的色氨酸衍生物，并在一系列不同的溶剂中测量了它们的发射光谱。本文介绍了这些新颖的树枝状结构的合成，并从溶剂和树枝状效应的角度讨论了它们的发射光谱。在第一系列的树枝状聚合物中，吲哚环的NH基团可用于氢键键合，而在第二系列中，吲哚的NH基团已转化为NMe。直接比较类似的NH和NMe衍生物的发射波长表明Kamlet-Taft溶剂beta3参数的重要性，该参数反映了溶剂接受NH基团氢键的能力，这对于NMe系列的NMe不可能。树状聚合物。对于NH树枝状聚合物 树突状壳与色氨酸亚基的连接导致发射波长发生红移。这种树枝状效应仅在非氢键溶剂中起作用。然而，对于NMe树枝状聚合物，树枝状壳的附着对吲哚环的发射光谱没有影响。这证明了在支链壳和吲哚NH基团之间的氢键键合在引起树突作用中的重要性。这是首次将树突作用明确分配给各个氢键相互作用，并表明这种分子内相互作用在树状聚合物中很重
• Towards a Series of Chiral Primary Amines Bearing α-Amino Acid and Benzo[d]imidazole Pendants, and Their Application in Asymmetric Aldol Reactions
  作者：Filip Bureš、Pravinkumar Mohite、Pavel Drabina

  DOI：10.1055/s-0036-1588107

  日期：——

  path towards chiral primary amines bearing α-amino acid and benzo[d]imidazole pendants has been developed. Six starting essential α-amino acids were converted into the target chiral amines in a four-step synthesis. The prepared amines were screened as organocatalysts in the direct asymmetric aldol reaction between 4-nitrobenzaldehyde or isatin and acetone or cyclohexanone. The aldol adducts were obtained

  摘要 已经开发出一种简单的反应路线，该路线指向带有α-氨基酸和苯并[ d ]咪唑侧基的手性伯胺。在四个步骤的合成中，将六个起始必需α-氨基酸转化为目标手性胺。在4-硝基苯甲醛或靛红与丙酮或环己酮之间的直接不对称醛醇缩合反应中，将制备的胺筛选为有机催化剂。以良好的化学收率，高达97：3的非对映选择性（与环己酮的反应）和高达71％ee的对映选择性获得醛醇加合物。三氟乙酸和苯甲酸被证明是分别在4-硝基苯甲醛和靛红上进行羟醛合成的最佳助催化剂。 已经开发出一种简单的反应路线，该路线指向带有α-氨基酸和苯并[ d ]咪唑侧基的手性伯胺。在四个步骤的合成中，将六个起始必需α-氨基酸转化为目标手性胺。在4-硝基苯甲醛或靛红与丙酮或环己酮之间的直接不对称醛醇缩合反应中，将制备的胺筛选为有机催化剂。以良好的化学收率，高达97：3的非对映选择性（与环己酮的反应）和高达71％ee的对映选择性获得醛醇加合物。三氟
• Synthesis of pyrroloindolines and furoindolines via cascade dearomatization of indole derivatives with carbenium ion
  作者：Chuan Liu、Qin Yin、Li-Xin Dai、Shu-Li You

  DOI：10.1039/c5cc00780a

  日期：——

  Intermolecular cascade dearomatization of substituted indoles with benzodithiolylium tetrafluoroborate has been developed, providing C3 methyl-substituted pyrroloindolines and furoindolines.

  用苯二硫代亚铁四氟硼酸盐对取代吲哚进行分子间级联脱芳构化反应，得到了C3甲基取代的吡咯吲哚烷和呋吲哚烷。
• Inverse γ-Turn-Inspired Peptide: Synthesis and Analysis of Segetalin A Indole Hemi­aminal
  作者：Matthias Lamping、Sebastian Enck、Armin Geyer

  DOI：10.1002/ejoc.201501179

  日期：2015.12

  Substitution of a peptide bond for an imine transforms the irreversible macrocyclization of peptides into a reversible process. The inherent cyclization tendency of a linear peptide is then analyzable through the equilibrium between the aldehyde and the imine by virtue of the higher reactivity of the corresponding linear peptide aldehyde. The tryptophan side chain of segetalin A aldehyde forms a 12-membered

  用肽键取代亚胺将肽的不可逆大环化转变为可逆过程。由于相应的线性肽醛具有较高的反应性，因此可以通过醛和亚胺之间的平衡来分析线性肽的固有环化趋势。segetalin A 醛的色氨酸侧链形成 12 元环状吲哚半胺醛，而不是预期的 18 元大环亚胺。在此，我们分析了这种不常见的半缩氨酸，表明环肽的生物合成不一定基于具有高固有大环内酰胺化趋势的线性前体肽。