tert-butoxycarbonyl-L-alanyl-D-isoglutamine | 18814-50-1

• 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: tert-butoxycarbonyl-L-alanyl-D-isoglutamine
• 英文别名: Boc-ala-D-Glu-NH2；(4R)-5-amino-4-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-5-oxopentanoic acid
• CAS: 18814-50-1
• 化学式: C₁₃H₂₃N₃O₆
• 分子量: 317.342
• InChiKey: HQRBWYFVNGVLSK-JGVFFNPUSA-N

物化性质

• 熔点：
  94-98 °C
• 沸点：
  636.3±55.0 °C(Predicted)
• 密度：
  1.231±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  148
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butoxycarbonyl-L-alanyl-D-isoglutamine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 生成 L-alanyl-D-iso-glutaminyl-γ-N-ε-benzyloxycarbonyl-L-lysinyl-D-alanyl-D-alanine benzyl ester trifluoroacetic acid salt
  参考文献：
  名称：

  Activation for Catalysis of Penicillin-Binding Protein 2a from Methicillin-Resistant Staphylococcus aureus by Bacterial Cell Wall

  摘要：

  Methicillin-resistant Staphylococcus aureus (MRSA) has acquired a unique penicillin-binding protein (PBP), PBP 2a, which has rendered the organism resistant to the action of all available beta-lactam antibiotics. The X-ray structure of PBP 2a shows the active site in a closed conformation, consistent with resistance to inhibition by beta-lactam antibiotics. However, it is known that PBP 2a avidly cross-links the S. aureus cell wall, which is its physiological function. It is shown herein that synthetic fragments of the bacterial cell wall bind in a saturable manner to PBP 2a and cause a conformational change in the protein that makes the active site more accessible to binding to a beta-lactam antibiotic. These observations and measurements point to a novel strategy by nature to keep the active site of PBP 2a sheltered from the inhibitory activity of the antibiotics, yet it becomes available to the polymeric cell wall by a requisite conformational change for the critical cell wall cross-linking reaction.

  DOI：

  10.1021/ja0434376
• 作为产物：
  描述：

  丁氧羰基-丙氨酸-D-谷氨酸-氨 生成 tert-butoxycarbonyl-L-alanyl-D-isoglutamine
  参考文献：
  名称：

  具有细菌细胞壁部分结构的 N-乙酰胞壁酰肽及其与免疫佐剂活性相关的类似物的化学合成

  摘要：

  为了阐明负责细菌细胞壁免疫佐剂活性的最小有效结构，合成了对应于金黄色葡萄球菌细胞壁部分结构的连续长度的 N-乙酰胞壁酰肽。鉴于发现 N-乙酰胞壁酰-L-丙氨酰-D-异谷氨酰胺是表现活性最少的结构部分，还合成了 N-乙酰胞壁酰氨基酸或 N-乙酰胞壁酰二肽的九种类似物。

  DOI：

  10.1246/bcsj.49.533

文献信息

• Synthesis and reactions of O-acetylated benzyl α-glycosides of 6-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-N-acetylmuramoyl-l-alanyl-d-isoglutamine esters: the base-catalysed isoglutamine ⇄ glutamine rearrangement in peptidoglycan-related structures
  作者：Dina Keglević、Andrew E. Derome

  DOI：10.1016/0008-6215(89)84005-4

  日期：1989.2

  Abstract Condensation of benzyl 2-acetamido-6- O -(2-acetamido-3,4,6-tri- O -acetyl-2-deoxy-3- O -[( R -1-carboxyethyl]-α- d -glucopyranoside ( 2 ) and its 4-acetate ( 4 ) with l -alanyl- d -isoglutamine benzyl ester via the mixed anhydride method yielded N -[2- O -[benzyl 2-acetamido-6- O -(2-acetamido-3,4,6-tri- O -acetyl-2-deoxy-β- d -glucopyranosyl)-2,3-dideoxy-α- d -glucopyranosid-3-yl]-( R )-

  5和6的O脱乙酰基化导致异谷氨酰胺残基的酯交换和α→γ酰胺化，得到N-[2- O-[苄基2-乙酰氨基-6- O-（2-乙酰氨基-2-脱氧-β- d-吡喃葡萄糖基）-2，3-二脱氧-α-d-吡喃葡萄糖苷-3-基]-（R）-乳酰基] -1-丙氨酰基-d-异谷氨酰胺甲酯（8）和​​-谷氨酰胺甲酯（9）。用MgO-甲醇处理6，在GlcNAc残基处引起脱乙酰基作用，得到N-[2- O-[苄基2-乙酰氨基-6-O-（2-乙酰氨基-2-脱氧-β-d-葡萄糖吡喃糖基）的混合物-4- O-乙酰基-2,3-二脱氧-α-d-吡喃葡萄糖苷-3-基]-（R）-乳酰基] -1-丙氨酰-d-异谷氨酰胺甲酯（11）和-谷氨酰胺甲酯（12 ）。肽聚糖相关结构的苄基或甲基酯保护与任何需要碱性介质的反应都不兼容。
• Synthesis of Bacterial-Derived Peptidoglycan Cross-Linked Fragments
  作者：Siavash Mashayekh、Klare L. Bersch、Jared Ramsey、Thomas Harmon、Benjamin Prather、Lauren A. Genova、Catherine L. Grimes

  DOI：10.1021/acs.joc.0c01852

  日期：2020.12.18

  bacterial cell wall. Fragments released from the PG serve as fundamental recognition elements for the immune system. The structure of the PG, however, encompasses a variety of chemical modifications among different bacterial species. Here, the applicability of organic synthetic methods to address this chemical diversity is explored, and the synthesis of cross-linked PG fragments, carrying biologically

  肽聚糖 (PG) 是细菌细胞壁的核心结构基序。从 PG 释放的片段是免疫系统的基本识别元件。然而，PG 的结构包含不同细菌物种之间的各种化学修饰。在这里，探讨了有机合成方法解决这种化学多样性的适用性，并使用溶液和固相方法介绍了带有生物相关氨基酸修饰和肽交联的交联 PG 片段的合成。
• Synthesis of Peptidoglycan Fragments from<i>Enterococcus faecalis</i>with Fmoc-Strategy for Glycan Elongation
  作者：Ning Wang、Hiroki Hasegawa、Cheng-yuan Huang、Koichi Fukase、Yukari Fujimoto

  DOI：10.1002/asia.201601357

  日期：2017.1.3

  Peptidoglycan (PGN) is an essential structural component of the bacterial cell wall conferring cell shape, which can be recognized by host‐recognition proteins and receptors as well as bacterial surface proteins. In this work, the PGN partial structures from Enterococcus faecalis that contain a tetrasaccharide and an octasaccharide with a unique heptapeptide were synthesized via an Fmoc‐strategy for

  肽聚糖（PGN）是赋予细胞形状的细菌细胞壁的重要结构成分，可以被宿主识别蛋白和受体以及细菌表面蛋白识别。在这项工作中，粪便肠球菌的PGN部分结构是通过Fmoc策略合成的，其中含有四糖和八糖以及独特的七肽，以延长聚糖链。也就是说，在这种有效的合成途径中，使用4'- O -Fmoc保护的二糖作为关键中间体来制备各种PGN片段。具有独特七肽的四糖和八糖都首次成功合成。
• Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides
  作者：Rosana Ribić、Ranko Stojković、Lidija Milković、Mariastefania Antica、Marko Cigler、Srđanka Tomić

  DOI：10.3762/bjoc.15.174

  日期：——

  lipophilic adamantane on N- or C-terminus through a glycolyl or hydroxyisobutyryl linker. Adjuvant activities of synthesized compounds were investigated in the mouse model using ovalbumin as an antigen. Their activities were compared to the previously described mannosylated adamantane-containing desmuramyl peptide and peptidoglycan monomer. Tested compounds exhibited adjuvant activity and the strongest enhancement

  村酰二肽是具有佐剂性质的肽聚糖的最小结构。更换N-乙酰基村m基部分和亲脂性的增加是制备具有改善的药理学性质的mu基二肽类似物的重要方法。存在于免疫感受态细胞上的甘露糖受体是模式识别受体，通过甘露糖配体的结合，它们会影响免疫系统。在这里，我们介绍了新型甘露糖基去村酰胺肽衍生物的设计，合成和生物学评估。甘露糖通过乙醇酰基或羟基异丁酰基接头与在N-或C-末端上含有亲脂性金刚烷的二肽偶联。使用卵清蛋白作为抗原，在小鼠模型中研究了合成化合物的佐剂活性。将它们的活性与先前描述的含甘露糖基的金刚烷的去马甲酰肽和肽聚糖单体进行比较。21（Man-OCH 2 - ᴅ-（1-Ad）Gly-ʟ-Ala-ᴅ-isoGln）。
• Synthesis of characteristic Mycobacterium peptidoglycan (PGN) fragments utilizing with chemoenzymatic preparation of meso-diaminopimelic acid (DAP), and their modulation of innate immune responses
  作者：Qianqian Wang、Yusuke Matsuo、Ambara R. Pradipta、Naohiro Inohara、Yukari Fujimoto、Koichi Fukase

  DOI：10.1039/c5ob02145f

  日期：——

  CharacteristicMycobacteriumpeptidoglycan fragments were comprehensively synthesized and their weaker immunostimulationviaNod1 and Nod2 was shown.

  特征性的分子Mycobacterium肽聚糖片段已全面合成，并显示了它们通过Nod1和Nod2较弱的免疫刺激作用。