Gly-CSA | 31060-88-5

• 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: Gly-CSA
• 英文别名: bis-(2-glycylamino-ethyl)-disulfide；N,N'-Bis-glycyl-cystamin；Bis-(2-glycylamino-aethyl)-disulfid；2-amino-N-[2-[2-[(2-aminoacetyl)amino]ethyldisulfanyl]ethyl]acetamide
• CAS: 31060-88-5
• 化学式: C₈H₁₈N₄O₂S₂
• 分子量: 266.389
• InChiKey: LRKUUOBDUCMAHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Gly-CSA 、 D-(-)-泛酰内酯 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以566 mg的产率得到N-pantoylglycyl-2-aminoethanethiol disulfide
  参考文献：
  名称：

  Metabolic Perturbation of an Essential Pathway: Evaluation of a Glycine Precursor of Coenzyme A

  摘要：

  Pantetheine and its corresponding disulfide pantethine play a key role in metabolism as building blocks of coenzyme A (CoA), an essential cofactor utilized in similar to 4% of primary metabolism and central to fatty acid, polyketide, and nonribosomal peptide synthases. Using a combination of recombinant engineering and chemical synthesis, we show that the disulfide of N-pantoylglycyl-2-aminoethanethiol (GlyPan), with one fewer carbon than pantetheine, can rescue a mutant E. coli strain MG1655 Delta panC lacking a functional pantothenate synthetase. Using mass spectrometry, we show that the GlyPan variant is accepted by the downstream CoA biosynthetic machinery, ultimately being incorporated into essential acyl carrier proteins. These findings point to further flexibility in CoA-dependent pathways and offer the opportunity to incorporate orthogonal analogues.

  DOI：

  10.1021/ja400795m
• 作为产物：
  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

文献信息

• 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。
• Surface Properties of Water-Soluble Glycine-Cysteamine-Protected Gold Clusters
  作者：Adam F. G. Leontowich、Christina F. Calver、Mita Dasog、Robert W. J. Scott

  DOI：10.1021/la902465b

  日期：2010.1.19

  We report the synthesis of water-soluble, nearly monodisperse glycine-ceysrtesamine (Gly-CSA) gold monolayer protected Clusters (MPCs) via base deprotection of Fmoc-Gly-CSA MPCs. terminal primary amine groups, are fully characterized by H-1 and C-13 NMR, UV-vis spectroscopy, and TEM, and their surface properties were probed by dynamic light scattering and acid-base titrations. The characterization methods indicate that the as-synthesized particles ire nearly monodisperse with all average particle size of 1.8 +/- 0.3 nm, but are only stable to aggregation in water at pHs of 4 and below. Acid-base titrations of the Gly-CSA MPCs show that the primary ammonium groups have a pK(a) of approximately 5.5, which is several orders of magnitude lower than the pK(a2) for the ammonium group of glycine (9.6). Thus, the particles are only partially protonated at intermediate pH's, which then drives the aggregation of the nanoparticles via hydrogen-bond formation. Dynamic light scattering results confirm the pH-driven aggregation of the nanoparticles, and studies with ninhydrin confirm that the primary amine groups are reactive and have potential for further functionalization. These results show that amine-terminated MPCs call be synthesized; however, their aggregation at intermediate pH's call limit their utility as building blocks for multifunctional nanoparticle syntheses.
• Fles; Markovac-Prpic, Arhiv za Kemiju, 1955, vol. 27, p. 211,213
  作者：Fles、Markovac-Prpic

  DOI：——

  日期：——
• Composition réductrice, pour déformation permanente des cheveux, contenant en tant qu'agent réducteur un amino mercaptoalkylamide ou l'un de ses sels, et son utilisation dans un procédé de déformation permanente des cheveux
  申请人：L'OREAL

  公开号：EP0432000B1

  公开（公告）日：1993-08-11