(S)-(2,2-dimethyl-1-methylcarbamoylpropyl)carbamic acid tert-butyl ester | 200865-04-9

• 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: (S)-(2,2-dimethyl-1-methylcarbamoylpropyl)carbamic acid tert-butyl ester
• 英文别名: (R)-tert-butyl 3,3-dimethyl-1-(methylamino)-1-oxobutan-2-ylcarbamate；Boc-Tle-NHMe；(2S)-2-tert-butoxycarbonylamino-3,3-dimethylbutanoic acid methylamide；(S)-Tert-Butyl (3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)carbamate；tert-butyl N-[(2S)-3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl]carbamate
• CAS: 200865-04-9
• 化学式: C₁₂H₂₄N₂O₃
• 分子量: 244.334
• InChiKey: BMDIHOPLEQXJHI-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  (S)-(2,2-dimethyl-1-methylcarbamoylpropyl)carbamic acid tert-butyl ester 在 N-羟基丁二酰亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.84h， 生成 L-亮氨酰-N,3-二甲基-L-缬氨酰胺
  参考文献：
  名称：

  Squaric Acid-Based Peptidic Inhibitors of Matrix Metalloprotease-1

  摘要：

  A series of squaric acid-peptide conjugates were synthesized and evaluated as inhibitors of MMP-1. The cyclobut-3-enedione core was substituted at the 3-position with several functional groups, such as -N(alkyl)OH, -NHOH, and -OH, that are designed to bind to the zinc atom in the active site of the metalloprotease. The 4-position of the cyclobut-3-enedione was derivatized with mono- or dipeptides that are designed to bind in the S1' and S2' subsites of the enzyme, and position the metal chelating group appropriately in the active site for binding to zinc. Positional scanning revealed that -N(Me)OH provided the highest level of inhibition among the chelating groups that were tested, and Leu-Tle-NHMe was the preferred amino acid sequence. A combination of these groups yielded an inhibitor with an IC50 value of 95 mu M. For one inhibitor, conversion of one of the carbonyl groups on the cyclobut-3-enedione core to a thiocarbonyl group resulted in a 18-fold increase in potency, and yielded a compound with an IC50 value of 15 mu M.

  DOI：

  10.1021/jo0517848
• 作为产物：
  描述：

  L-叔亮氨酸 在 三乙胺 、 N,N'-羰基二咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 (S)-(2,2-dimethyl-1-methylcarbamoylpropyl)carbamic acid tert-butyl ester
  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

文献信息

• l-tert-Leucine-Derived AmidPhos–Silver(I) Chiral Complexes for the Asymmetric [3+2] Cycloaddition of Azomethine Ylides
  作者：Haifei Wang、Zhipeng Zhou、Xiaojun Zheng、Jialin Liu、Jinlei Li、Pushan Wen

  DOI：10.1055/s-0036-1588137

  日期：——

  The l -tert-leucine-derived AmidPhos/silver(I) catalytic system has been developed for the asymmetric [3+2] cycloaddition of azomethine ylides with electronic-deficient alkenes with or without Et3N. Under optimal conditions, highly functionalized endo-4-pyrrolidines were obtained with modest to high yields (up to 99% yield) and enantioselectivities (up to 98% ee).

  L-叔亮氨酸衍生的 AmidPhos/silver(I) 催化体系已开发用于在有或没有 Et3N 的情况下，偶氮甲碱叶立德与缺电子烯烃的不对称 [3+2] 环加成反应。在最佳条件下，以中等至高产率（高达 99% 的产率）和对映选择性（高达 98% ee）获得高度官能化的内 4-吡咯烷。
• Stereoselective nucleophilic addition to imines catalyzed by chiral bifunctional thiourea organocatalysts
  作者：Alessandra Puglisi、Maurizio Benaglia、Rita Annunziata、Davide Rossi

  DOI：10.1016/j.tetasy.2008.09.030

  日期：2008.10

  such bifunctional chiral molecules, either neutral or protonated species, was investigated in the addition of acetylacetone to β-nitrostyrene as a model reaction. Using the best conditions, high yields and enantioselectivities of up to 85% were obtained. The same metal free catalysts were then employed in the addition of activated nucleophiles to imines: in the reaction of 1,3-diketones with N-CBz imines

  通过（S）-t-亮氨酸衍生物与（1 R，2 R）-反式结合获得的新手性双功能有机催化剂的合成开发了-1，2-二氨基-环己烷。已经成功地合成了几种化合物，它们代表通过手性主链连接的含有硫脲基和叔氨基的一类有机催化剂。在模型反应中，向β-硝基苯乙烯中添加了乙酰丙酮，研究了这种中性或质子化双功能手性分子的催化行为。在最佳条件下，可获得高达85％的高收率和对映选择性。然后将相同的不含金属的催化剂用于向亚胺中添加活化的亲核试剂：在1,3-二酮与N -CBz亚胺的反应中，分离出的产物的收率高达61％ee，而与丙二酸二乙酯的反应则被分离出来。对映选择性高达71％。
• Catalytic Enantioselective Synthesis of Pyridyl Sulfoximines
  作者：Yu Tang、Scott J. Miller

  DOI：10.1021/jacs.1c04431

  日期：2021.6.23

  past decades, whereas limited reports exist for their synthesis via asymmetric catalysis. We report the synthesis of chiral sulfoximines through the desymmetrizing N-oxidation of pyridyl sulfoximines using an aspartic acid-containing peptide catalyst. Various mono- and bis-pyridyl sulfoximine oxides are obtained with up to 99:1 er. The directing group introduced on the substrate highly enhances the

  亚砜亚胺具有独特的化学和生物活性，在过去几十年中引起了极大的关注，而通过不对称催化合成它们的报道有限。我们报告了通过使用含天冬氨酸的肽催化剂对吡啶基亚砜亚胺进行去对称N-氧化来合成手性亚砜亚胺。以高达 99:1 的 er 获得各种单和双吡啶基亚砜亚胺氧化物。在底物上引入的导向基团高度增强了对映诱导，并且可以很容易地去除以产生游离的 N-H 亚砜亚胺。此外，具有甲酯和甲基酰胺C端保护基团的肽产生产物的相反对映异构体。提出了一种结合模型来解释这种现象。
• ADAM10 and its Uses Related to Infection
  申请人：Rubin Donald H.

  公开号：US20090220514A1

  公开（公告）日：2009-09-03

  The present invention relates to a protein, ADAM10, ADAM10 nucleic acid sequences and ADAM10 proteins encoded by these sequences that are involved in infection by one or more pathogen such as a virus, a parasite, a bacteria or a fungus or are otherwise associated with the life cycle of a pathogen.

  本发明涉及一种蛋白质ADAM10，ADAM10核酸序列和由这些序列编码的ADAM10蛋白质，它们参与感染一种或多种病原体，例如病毒、寄生虫、细菌或真菌，或与病原体的生命周期有关。
• ADAM10 and its uses related to infection
  申请人：Vanderbilt University

  公开号：US08247451B2

  公开（公告）日：2012-08-21

  The present invention relates to a protein, ADAM10, ADAM10 nucleic acid sequences and ADAM10 proteins encoded by these sequences that are involved in infection by one or more pathogen such as a virus, a parasite, a bacteria or a fungus or are otherwise associated with the life cycle of a pathogen.

  本发明涉及一种蛋白质ADAM10、ADAM10核酸序列以及由这些序列编码的ADAM10蛋白质，它们参与一种或多种病原体（如病毒、寄生虫、细菌或真菌）的感染，或者与病原体的生命周期有关。