S-propargyl-N-[(1,1-dimethylethoxy)carbonyl]-L-cysteine methyl ester | 1262387-74-5

• 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-propargyl-N-[(1,1-dimethylethoxy)carbonyl]-L-cysteine methyl ester
• 英文别名: methyl (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-prop-2-ynylsulfanylpropanoate
• CAS: 1262387-74-5
• 化学式: C₁₂H₁₉NO₄S
• 分子量: 273.353
• InChiKey: YWSCGLOUKKDFJT-VIFPVBQESA-N

物化性质

• 沸点：
  391.6±42.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  S-propargyl-N-[(1,1-dimethylethoxy)carbonyl]-L-cysteine methyl ester 以66%的产率得到(R)-2-氨基-3-(2-丙炔基巯基)丙酸
  参考文献：
  名称：

  Neoglycopeptides through direct functionalization of cysteine

  摘要：

  Neoglycopeptides are readily prepared by direct functionalization of cysteine-containing peptides followed by click triazole formation between the resulting propargylated peptides and protected or free (2-azido)-ethyl gluco-, manno,- and galactopyranosides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.021
• 作为产物：
  描述：

  N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester 、 3-溴丙炔 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以55%的产率得到S-propargyl-N-[(1,1-dimethylethoxy)carbonyl]-L-cysteine methyl ester
  参考文献：
  名称：

  Neoglycopeptides through direct functionalization of cysteine

  摘要：

  Neoglycopeptides are readily prepared by direct functionalization of cysteine-containing peptides followed by click triazole formation between the resulting propargylated peptides and protected or free (2-azido)-ethyl gluco-, manno,- and galactopyranosides. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.021

文献信息

• ‘Click’ glycosylation of peptides through cysteine propargylation and CuAAC
  作者：Sandrine Lamandé-Langle、Charlotte Collet、Raphaël Hensienne、Christine Vala、Françoise Chrétien、Yves Chapleur、Amel Mohamadi、Patrick Lacolley、Véronique Regnault

  DOI：10.1016/j.bmc.2014.09.056

  日期：2014.12

  'Click' glycosylation of cysteine-containing peptides were carried out in good yield by Copper(I)-catalyzed Azide-Alkyne Cycloaddition (CuAAC). For that peptides were functionalized though direct propargylation of the cysteine residue allowing their use in CuAAC with suitable free or protected azido sugars of gluco, manno and galacto configuration. Among these free and protected glycopeptides a series of 'glycoRGD' peptides were obtained and submitted to in vitro platelet aggregation tests, showing that the pseudoglycosylation of the adhesion sequence lowers the IC50 value and thus could improve the in vivo pharmacokinetic properties. (C) 2014 Elsevier Ltd. All rights reserved.

  半胱氨酸肽通过Cu(I)催化的叠氮化物-炔烃环加成(CuAAC)实现了"点击"糖基化，产率良好。此方法中，肽通过半胱氨酸残基的直接炔基化进行官能化，使其可用于与具有gluco、manno和galacto构型的合适叠氮化糖（自由或保护状态）进行CuAAC反应。在所获得的自由和保护型糖肽中，一系列"glycoRGD"肽被制备并进行了体外血小板聚集测试，结果显示伪糖基化的黏附序列降低了IC50值，从而可能改善体内药代动力学特性。©2014 Elsevier Ltd. 保留所有权利。
• An Enantioselective Recyclable Polystyrene-Supported Threonine-Derived Organocatalyst for Aldol Reactions
  作者：Andrea H. Henseler、Carles Ayats、Miquel A. Pericàs

  DOI：10.1002/adsc.201400033

  日期：2014.5.26

  amino acids covalently supported onto polystyrene through alkyne–azide cycloaddition reactions has been synthesized and evaluated as catalysts in asymmetric aldol reactions. A polymer‐supported threonine behaves as an easily recyclable, highly reactive and stereoselective (up to 99% ee) catalyst in the aldol reaction of both cyclic and acyclic ketone donors with aromatic aldehydes in aqueous environments

  合成了一系列通过炔-叠氮化物环加成反应共价负载在聚苯乙烯上的伯氨基酸，并作为不对称羟醛反应的催化剂进行了评估。在水性环境中，环状和非环状酮供体与芳族醛的醛醇缩合反应中，聚合物负载的苏氨酸可作为易于回收，高反应性和立体选择性（高达99％ee）的催化剂。而环状酮与反应反非对映选择性，顺式加成物主要与无环的基材而获得。苏氨酸杂化催化剂已用于对映纯的醛醇缩醛产物的小型文库的顺序合成。
• Protein modification via alkyne hydrosilylation using a substoichiometric amount of ruthenium(<scp>ii</scp>) catalyst
  作者：Terence T.-L. Kwan、Omar Boutureira、Elizabeth C. Frye、Stephen J. Walsh、Moni K. Gupta、Stephen Wallace、Yuteng Wu、Fengzhi Zhang、Hannah F. Sore、Warren R. J. D. Galloway、Jason W. Chin、Martin Welch、Gonçalo J. L. Bernardes、David R. Spring

  DOI：10.1039/c6sc05313k

  日期：——

  The development of site-specific modification of alkyne-functionalized proteins using dimethylarylsilanes and substoichiometric or low-loading of Ru(ii) catalysts is reported. Furthermore, the resultant gem-vinylsilane can undergo further targeted chemical modifications, highlighting its potential for single-site, dual-modification applications.

  报道了使用二甲基芳基硅烷和亚化学计量或低负载Ru(ii)催化剂对炔基化蛋白质进行位点特异性修饰的研究。此外，所得到的宝石烯基硅烷可以进一步进行有针对性的化学修饰，突显其在单位点、双重修饰应用方面的潜力。
• Biosynthetic diversification of non-ribosomal peptides through activity-based protein profiling of adenylation domains
  作者：Fumihiro Ishikawa、Natsumi Tsukumo、Erika Morishita、Shumpei Asamizu、Saaya Kusuhara、Shinsuke Marumoto、Katsuki Takashima、Hiroyasu Onaka、Genzoh Tanabe

  DOI：10.1039/d3cc02633g

  日期：——

  Coupled with precursor-directed biosynthesis, activity-based protein profiling of non-ribosomal peptide synthetases provides rational guidance for the biosynthetic diversification of non-ribosomal peptides.

  与前体定向生物合成相结合，基于活性的非核糖体肽合成酶蛋白质分析为非核糖体肽的生物合成多样化提供了合理的指导。
• Metal-free synthesis of E-vinylphosphonates via photoinduced alkyne hydrophosphonylation and thiol promoted isomerization sequence
  作者：Samuele Staderini、Alessandro Dondoni、Alberto Marra

  DOI：10.1016/j.tetlet.2014.11.099

  日期：2015.1

  The alkyne hydrophosphonylation is an atom economical method for the synthesis of vinylphosphonates that are compounds of both biological and synthetic relevance. Recent approaches based on the use of metal catalysts have only partially solved the problems of the reaction selectivity as well as of economical and large amount production. We report in this Letter on a metal-free approach that leads to E-vinylphosphonates in high yields. The approach is based on a two-step one-pot synthesis, namely: (a) photoinduced anti-Markovnikov addition of a H-phosphonate to alkynes to give mixtures of E- and Z-vinylphosphonates, and (b) cysteine promoted photoinduced conversion of the crude mixtures of adducts into E-isomers (58-92% overall yields). (C) 2014 Elsevier Ltd. All rights reserved.