(2R,3R)-4-amino-4-deoxy-2,3-O-isopropylidene-D-erythronic acid | 18908-37-7

• 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: (2R,3R)-4-amino-4-deoxy-2,3-O-isopropylidene-D-erythronic acid
• 英文别名: (4R,5R)-5-(aminomethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylic acid
• CAS: 18908-37-7
• 化学式: C₇H₁₃NO₄
• 分子量: 175.185
• InChiKey: HOSMNRMCUONPEZ-RFZPGFLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  81.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3R)-4-amino-4-deoxy-2,3-O-isopropylidene-D-erythronic acid 以97%的产率得到2,2-dimethyl-(3ar,6ac)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-one
  参考文献：
  名称：

  由手性和非手性聚乙烯吡咯烷酮稳定的双金属纳米团簇的合成和表征。催化 C(sp3)–H 氧化

  摘要：

  第二代手性取代的聚-N-乙烯基吡咯烷酮(CSPVPs) (-)- 1R和(+)- 1S通过(3a R ,6a R )- 和(3a S ,6a S )-的自由基聚合合成5-ethenyl-tetrahydro-2,2-dimethyl-4 H -1,3-dioxolo[4,5- c ]pyrrol-4-one，分别使用热和光化学反应。它们分别由d-异抗坏血酸和d-核糖生产。此外，手性聚合物(-)- 2也由( S )聚合合成。)-3-(甲氧基甲氧基)-1-vinylpyrrolidin-2-one。使用 HRMS 测量这些手性聚合物的分子量，并使用13 C NMR 光谱研究聚合物链的立构规整度。手性聚合物 (-)- 1R、 (+)- 1S和 (-)- 2以及聚-N-乙烯基吡咯烷酮 (PVP, MW 40K) 分别用于稳定 Cu/Au 或 Pd/Au 纳米团簇。(-)- 1R和(+)- 1S稳定的双金属纳米团簇的CD光谱在波长

  DOI：

  10.1021/acs.joc.2c00449
• 作为产物：
  描述：

  D-erythronolactone acetonide 在 肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3R)-4-amino-4-deoxy-2,3-O-isopropylidene-D-erythronic acid
  参考文献：
  名称：

  仲氨基醇：亲和力捕获和释放中使用的无痕可裂解连接子。

  摘要：

  肽的捕获和释放通常是发现具有新颖功能的物质的途径中的关键操作。但是，有效捕获的最佳方法阻碍了释放。为了克服这一挑战，我们报道了基于仲氨基醇的接头，可在捕获后释放肽。这些氨基醇基于丝氨酸（seramox）或异丝氨酸（isoseramox），可以在固相肽合成过程中通过还原胺化将其掺入肽中。在NaIO 4下几分钟内，两个接头都被定量切割治疗。异麦角菌酯的切割产生天然肽N-末端。该连接物还显示出广泛的底物相容性。并入合成肽库后，可通过nanoLC-MS / MS鉴定所有序列。接头是细胞相容的。含有该接头的穿透细胞的肽在摄入细胞后被有效捕获并鉴定。这些发现表明，这种基于仲氨基醇的接头可能是肽发现平台的合适工具。

  DOI：

  10.1002/anie.202003478

文献信息

• Secondary Amino Alcohols: Traceless Cleavable Linkers for Use in Affinity Capture and Release
  作者：Sebastian Pomplun、Christopher R. Shugrue、Adeline M. Schmitt、Carly K. Schissel、Charlotte E. Farquhar、Bradley L. Pentelute

  DOI：10.1002/anie.202003478

  日期：2020.7.6

  with novel functions. However, the best methods for efficient capture impede facile release. To overcome this challenge, we report linkers based on secondary amino alcohols for the release of peptides after capture. These amino alcohols are based on serine (seramox) or isoserine (isoseramox) and can be incorporated into peptides during solid‐phase peptide synthesis through reductive amination. Both

  肽的捕获和释放通常是发现具有新颖功能的物质的途径中的关键操作。但是，有效捕获的最佳方法阻碍了释放。为了克服这一挑战，我们报道了基于仲氨基醇的接头，可在捕获后释放肽。这些氨基醇基于丝氨酸（seramox）或异丝氨酸（isoseramox），可以在固相肽合成过程中通过还原胺化将其掺入肽中。在NaIO 4下几分钟内，两个接头都被定量切割治疗。异麦角菌酯的切割产生天然肽N-末端。该连接物还显示出广泛的底物相容性。并入合成肽库后，可通过nanoLC-MS / MS鉴定所有序列。接头是细胞相容的。含有该接头的穿透细胞的肽在摄入细胞后被有效捕获并鉴定。这些发现表明，这种基于仲氨基醇的接头可能是肽发现平台的合适工具。
• CHIRAL-SUBSTITUTED POLY-N-VINYLPYRROLIDINONES AND COMPLEXES WITH BIMETALLIC NANOCLUSTERS AND USES THEREOF IN ASYMMETRIC OXIDATION REACTIONS
  申请人：Kansas State University Research Foundation

  公开号：US20220204447A1

  公开（公告）日：2022-06-30

  Chiral polyvinylpyrrolidinone (CSPVP), complexes of CSPVP with a core species, such as a bimetallic nanocluster catalyst, and enantioselective oxidation reactions utilizing such complexes are disclosed. The catalytic complexes have exhibited the ability to achieve reaction products have a very high degree of optical purifies. These reaction products can be used as reagents in the synthesis of complex organic molecules, such as bioactive products, and C—H bond oxidation of complex molecules including various drugs and natural products.

  本发明公开了手性聚乙烯吡咯烷酮（CSPVP）及其与核心物种（例如双金属纳米簇催化剂）的配合物，以及利用这些配合物进行对映选择性氧化反应。这些催化配合物已经表现出实现反应产物具有非常高的光学纯度的能力。这些反应产物可用作复杂有机分子（如生物活性产物）的合成试剂，并用于包括各种药物和天然产物在内的复杂分子的C-H键氧化。
• Class I Major Histocompatibility Complexes Loaded by a Periodate Trigger
  作者：Boris Rodenko、Mireille Toebes、Patrick H. N. Celie、Anastassis Perrakis、Ton N. M. Schumacher、Huib Ovaa

  DOI：10.1021/ja9037565

  日期：2009.9.2

  Class I major histocompatibility complexes (MHCs) present peptide ligands on the cell surface for recognition by appropriate cytotoxic T cells. The unstable nature of unliganded MHC necessitates the production of recombinant class I complexes through in vitro refolding reactions in the presence of an added excess of peptides. This strategy is not amenable to high-throughput production of vast collections of class I complexes. To address this issue, we recently designed photocaged MHC ligands that can be cleaved by a UV light trigger in the MHC bound state under conditions that do not affect the integrity of the MHC structure. The results obtained with photocaged MHC ligands demonstrate that conditional MHC ligands can form a generally applicable concept for the creation of defined peptide-MHCs. However, the use of UV exposure to mediate ligand exchange is unsuited for a number of applications, due to the lack of UV penetration through cell culture systems and due to the transfer of heat upon UV irradiation, which can induce evaporation. To overcome these limitations, here, we provide proof-of-concept for the generation of defined peptide-MHCs by chemical trigger-induced ligand exchange. The crystal structure of the MHC with the novel chemosensitive ligand showcases that the ligand occupies the expected binding site, in a conformation where the hydroxyl groups should be reactive to periodate. We proceed to validate this technology by producing peptide-MHCs that can be used for T cell detection. The methodology that we describe here should allow loading of MHCs with defined peptides in cell culture devices, thereby permitting antigen-specific T cell expansion and purification for cell therapy. In addition, this technology will be useful to develop miniaturized assay systems for performing high-throughput screens for natural and unnatural MHC ligands.
• Synthesis of anthopleurine, the alarm pheromone from Anthopleura elegantissima
  作者：James A. Musich、Henry Rapoport

  DOI：10.1021/ja00483a037

  日期：1978.7
• SOLUTION-PHASE AFFINITY SELECTION OF INHIBITORS FROM COMBINATORIAL PEPTIDE LIBRARIES
  申请人：Massachusetts Institute of Technology

  公开号：US20190300576A1

  公开（公告）日：2019-10-03

  The present invention provides novel peptides (e.g., peptides, macrocyclic peptides, mini-proteins) that modulate protein-protein interactions or salts thereof, and methods of making and using the inventive peptides. In some embodiments, the peptides are high affinity inhibitors (e.g., K D of at most 100 nM, at most 10 nM, at most 1 nM) of a protein-protein interaction. In certain embodiments, these peptides interfere with p53-MDM2 binding interactions (e.g., by binding to MDM2 (GenBank® Gene ID: 4193)). In some embodiments, the peptides interfere with the dimerization of the C-terminal domain of the human immunodeficiency virus (HIV) capsid protein (C-CA), comprising residues 146-231 of the HIV capsid protein (e.g., by binding to the C-terminal domain of the HIV capsid protein (C-CA), thereby inhibiting the dimeric interface of HIV capsid protein, thereby inhibiting viral assembly). These inventive peptides were rapidly generated and identified using novel methods described herein comprising combinatorial peptide synthesis and/or solution affinity selection.