N,N'-bis<(tert-butyloxycarbonyl)glycyl>cystamine | 97314-11-9

• 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: N,N'-bis<(tert-butyloxycarbonyl)glycyl>cystamine
• 英文别名: [Boc-Gly-CSA]2；Boc-Gly-CSA；[Boc-Gly-cysteamine]2；tert-butyl N-[2-[2-[2-[[2-[(2-methylpropan-2-yl)oxycarbonylamino]acetyl]amino]ethyldisulfanyl]ethylamino]-2-oxoethyl]carbamate
• CAS: 97314-11-9
• 化学式: C₁₈H₃₄N₄O₆S₂
• 分子量: 466.623
• InChiKey: OMUBLDOVSMDJNE-UHFFFAOYSA-N

物化性质

• 熔点：
  98-100 °C
• 沸点：
  710.9±60.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  186
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N'-bis<(tert-butyloxycarbonyl)glycyl>cystamine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 Gly-CSA
  参考文献：
  名称：

  Chemical functionalization and modification of surface-bound cystamine–glycine monolayers on gold nanoparticles

  摘要：

  在此，我们报告了用甘氨酸-胱胺（Gly-CSA）稳定基团进行表面修饰的金纳米粒子的合成、表征和后功能化。我们的研究表明，金单层保护团簇（MPCs）可通过布氏-施氏法（Brust-Schiffrin method）使用 Boc-Gly-CSA 稳定剂合成，然后用三氟乙酸有效去除 Boc 保护基团。我们通过紫外-可见光、TEM 和 1H NMR 对得到的 Gly-CSA Au MPC 进行了表征，它们在溶液中长期保持稳定。最后，我们展示了使用硬脂酸活化酯和 Bodipy 染料衍生物可对 Gly-CSA Au MPCs 进行进一步功能化，其产量几乎达到了等比级数。因此，这项工作为改变 MPCs 的表面化学性质提供了另一种通用方法。

  DOI：

  10.1139/v08-025
• 作为产物：
  描述：

  BOC-甘氨酸-N-羟基琥柏酰亚胺酯 、 cystamine dihydrochioride 在 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 12.0h， 生成 N,N'-bis<(tert-butyloxycarbonyl)glycyl>cystamine
  参考文献：
  名称：

  Combinatorial Synthesis through Disulfide Exchange: Discovery of Potent Psammaplin A Type Antibacterial Agents Active against Methicillin-ResistantStaphylococcus aureus (MRSA)

  摘要：

  Psammaplin A is a symmetrical bromotyrosine -derived disulfide natural product isolated from the Psammaplysilla sponge, which exhibits in vitro antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). Inspired by the structure of this marine natural product, a combinatorial scrambling strategy for the construction of heterodimeric disulfide analogues was developed and applied to the construction of a 3828-membered library starting from 88 homodimeric disulfides. These psammaplin A analogues were screened directly against various gram positive bacterial strains leading to the discovery of a series of potent antibacterial agents active against methicillin-resistant Staphylococcus aureus (MRSA), Among the most active leads derived from these studies are compounds 104. 105, 113, 115, 123, and 128. The present, catalytically-induced. disulfide exchange strategy may be extendable to other types of building blocks bearing thiol groups facilitating the construction of diverse discovery-oriented combinatorial libraries.

  DOI：

  10.1002/1521-3765(20011001)7:19<4280::aid-chem4280>3.0.co;2-3

文献信息

• Ferrocenoyl glycylcystamine: organization into a supramolecular helicate structure
  作者：Irene Bediako-Amoa、Roberta Silerova、Heinz-Bernhard Kraatz

  DOI：10.1039/b206647e

  日期：2002.10.11

  Extensive intermolecular hydrogen bonding in ferrocenoyl glycylcystamine gives rise to a novel ordered double helical arrangement with a helical pitch height of 14 Å.

  二茂铁酰基甘氨酰胱胺中广泛的分子间氢键产生了一种新颖的有序双螺旋排列，螺距高度为 14 Å。
• Synthesis, structure and electrochemistry of ferrocene–peptide macrocycles
  作者：Somenath Chowdhury、Gabriele Schatte、Heinz-Bernhard Kraatz

  DOI：10.1039/b401039f

  日期：——

  Redox active cyclopeptides Fc[CSA]2 (5), Fc[Gly–CSA]2 (6), Fc[Ala–CSA]2 (7), Fc[Val–CSA]2 (8) and Fc[Leu–CSA]2 (9) (CSA = cysteamine) which are formed by the reaction of ferrocenedicarboxylic acid with peptide cystamines at high dilutions. These systems exhibit H-bonding involving the amide NH in solution as shown by their temperature dependent NMR spectra. With the exception of 5, the ferrocene macrocycles display intramolecular N⋯O cross-ring H-bonding in the solid state involving the amino acids proximal to the ferrocene.

  氧化还原活性环肽 Fc[CSA]2 (5)、Fc[GlyâCSA]2 (6)、Fc[AlaâCSA]2 (7)、Fc[ValâCSA]2 (8) 和 Fc[LeuâCSA]2 (9)（CSA = 半胱胺）是二茂铁二羧酸与肽胱胺在高稀释度下反应生成的。这些体系在溶液中表现出涉及酰胺 NH 的 H 键，这一点可以从它们与温度相关的 NMR 光谱中看出。除 5 外，二茂铁大环在固态下显示出分子内 Nâ¯O 跨环 H 键，涉及二茂铁附近的氨基酸。
• Chemical functionalization and modification of surface-bound cystamine–glycine monolayers on gold nanoparticles
  作者：Mita Dasog、Amir Kavianpour、Matthew F Paige、Heinz-Bernhard Kraatz、Robert W.J. Scott

  DOI：10.1139/v08-025

  日期：2008.5.1

  Herein, we report the synthesis, characterization, and post-functionalization of Au nanoparticles that have been surface-modified with glycine–cystamine (Gly-CSA) stabilizing groups. We show that Au monolayer protected clusters (MPCs) can be synthesized via the Brust–Schiffrin method using a Boc-Gly–CSA stabilizer, followed by efficient removal of the Boc protecting group with trifluoroacetic acid. The resulting Gly–CSA Au MPCs are characterized via UV–vis, TEM, and ¹H NMR, and are stable in solution over long periods of time. Finally, we show that the Gly–CSA Au MPCs can be further functionalized with nearly stoichiometric yields using activated esters of stearic acid and a Bodipy dye derivative. Thus, this work provides an alternative, general approach for the modification of the surface chemistry of MPCs.Key words: gold nanoparticles, peptide stabilizers, dyes.

  在此，我们报告了用甘氨酸-胱胺（Gly-CSA）稳定基团进行表面修饰的金纳米粒子的合成、表征和后功能化。我们的研究表明，金单层保护团簇（MPCs）可通过布氏-施氏法（Brust-Schiffrin method）使用 Boc-Gly-CSA 稳定剂合成，然后用三氟乙酸有效去除 Boc 保护基团。我们通过紫外-可见光、TEM 和 1H NMR 对得到的 Gly-CSA Au MPC 进行了表征，它们在溶液中长期保持稳定。最后，我们展示了使用硬脂酸活化酯和 Bodipy 染料衍生物可对 Gly-CSA Au MPCs 进行进一步功能化，其产量几乎达到了等比级数。因此，这项工作为改变 MPCs 的表面化学性质提供了另一种通用方法。
• Method of coupling polysaccharides to proteins
  申请人：DE STAAT DER NEDERLANDEN VERTEGENWOORDIGD DOOR DE MINISTER VAN WELZIJN, VOLKSGEZONDHEID EN CULTUUR

  公开号：EP0848011A1

  公开（公告）日：1998-06-17

  A novel method of covalently coupling polysaccharides to other biopolymers is provided, using an amino-thiol linker represented by formula 1         H2N-[(CH2)m-CHR1-CR2R3-A]q-CHR4-(CHR5)p-CHR6-S-R7     1 wherein A is a direct bond or a group having the formula         -Z-(CH2)m-CHR1-CHR2R3}nZ-, m is an integer from 0 to 5; n is an integer from 0 to 3; p is an integer from 0 to 2; q is the integer 0 or 1; R1 is hydrogen or C1-C6 alkyl, optionally substituted by amino, hydroxyl, carboxyl, C1-C4 alkoxycarbonyl, carbamoyl, mono- or di-C1-C4-alkylcarbamoyl or N-(α-carboxyalkyl)carbamoyl, or, if m ≠ 0, R1 is hydroxyl, amino or peptidyl-amino; R2 and R3 are independently hydrogen or C1-C4 alkyl, or together form an oxo group; R4 is hydrogen, C1-C4 alkyl, carboxyl, C1-C4 alkoxycarbonyl, carbamoyl, mono- or di-C1-C4-alkylcarbamoyl or N-(α-carboxyalkyl)carbamoyl; R5 is hydrogen, methyl, hydroxy or C1-C7 acyloxy; R6 is hydrogen or methyl; R7 is hydrogen or a thiol-protecting group or a group having the formula         -S-CHR6-(CHR5)p-CHR4-[A-CR2R3-CHR1-(CH2)m]q-NH2; and Z is imino, methylimino, oxygen or sulphur.

  提供了一种将多糖与其他生物聚合物共价偶联的新方法，使用了由式 1 表示的氨基硫醇连接剂 H2N-[(CH2)m-CHR1-CR2R3-A]q-CHR4-(CHR5)p-CHR6-S-R7 1 其中 A 是直接键或具有以下式子的基团 -Z-(CH2)m-CHR1-CHR2R3}nZ-, m 是 0 至 5 的整数； n 是 0 至 3 的整数； p 是 0 至 2 的整数； q 是 0 或 1 的整数； R1 是氢或 C1-C6 烷基，任选被氨基、羟基、羧基、C1-C4 烷氧基羰基、氨基甲酰基、单-或二-C1-C4-烷基氨基甲酰基或 N-(α-羧基烷基)氨基甲酰基取代，或者，如果 m≠0，R1 是羟基、氨基或肽基氨基； R2 和 R3 独立地为氢或 C1-C4 烷基，或共同形成一个氧代基团； R4 是氢、C1-C4-烷基、羧基、C1-C4-烷氧基羰基、氨基甲酰基、单-或双-C1-C4-烷基氨基甲酰基或 N-（α-羧基烷基）氨基甲酰基； R5 是氢、甲基、羟基或 C1-C7 乙酰氧基； R6 是氢或甲基 R7 是氢或硫醇保护基团或具有以下式子的基团 -S-CHR6-(CHR5)p-CHR4-[A-CR2R3-CHR1-(CH2)m]q-NH2; and Z 是亚氨基、甲基亚氨基、氧或硫。
• Synthesis and radioprotective activity of new cysteamine and cystamine derivatives
  作者：J. Oiry、J. Y. Pue、J. L. Imbach、M. Fatome、H. Sentenac-Roumanou、C. Lion

  DOI：10.1021/jm00161a015

  日期：1986.11

  A variety of N-(aminoalkanoyl)-S-acylcysteamine and N,N'-bis(aminoalkanoyl)cystamine salt derivatives were synthesized. Toxicity and radioprotective activity (as the dose reduction factor DRF) were determined in vivo on mice and compared to WR 2721 and S-acetylcysteamine hydrochloride. One of the most interesting compounds of this series was N-glycyl-S-acetylcysteamine trifluoroacetate (16, I 102). Structure-activity relationships are discussed.