D-谷氨酸双苄酯对甲苯磺酸盐 | 19898-41-0

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 谷氨酸类衍生物
• 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
• 中文名称: D-谷氨酸双苄酯对甲苯磺酸盐
• 中文别名: D-谷氨酸二苄酯对甲苯磺酸盐
• 英文名称: H-D-Glu(Bzl)OBzl * p-toluenesulphonic acid
• 英文别名: dibenzyl D-glutamate p-toluenesulfonic acid salt；D-glutamic acid dibenzyl ester p-toluenesulfonate；dibenzyl D-glutamate p-toluenesulfonate；dibenzyl L-glutamate p-toluenesulfonate；D-glutamic acid dibenzyl ester p-toluenesufonate salt；D-glutamic acid dibenzyl ester 4-toluenesulfonate；D-glutamate dibenzylester p-toluenesulfonate；D-Glutaminsaeure-dibenzylester；H-D-Glu(OBn)-OBn*p-tosylate；H-D-Glu(obzl)-obzl P-tosylate；dibenzyl (2R)-2-aminopentanedioate;4-methylbenzenesulfonic acid
• CAS: 19898-41-0
• 化学式: C₇H₈O₃S*C₁₉H₂₁NO₄
• 分子量: 499.585
• InChiKey: HVZUAIVKRYGQRM-UNTBIKODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: H-D-Glu(OBzl)-OBzl p-tosylate
Synonyms: D-Glutamic acid dibenzyl ester p-toluenesulfonate

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: H-D-Glu(OBzl)-OBzl p-tosylate
CAS number: 19898-41-0

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C19H21NO4.C7H8O3S
Molecular weight: 499.6

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, sulfur oxides.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  D-谷氨酸双苄酯对甲苯磺酸盐 在 盐酸 、 palladium 10% on activated carbon 、 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 160.42h， 生成 N-{2-O-[2-acetamido-1,2,5-trideoxy-1,5-imino-D-glucitol-3-yl]-D-lactoyl}-L-alanyl-D-glutamate hydrochloride
  参考文献：
  名称：

  Inhibitors for Bacterial Cell-Wall Recycling

  摘要：

  Gram-negative bacteria have evolved an elaborate process for the recycling of their cell wall, which is initiated in the periplasmic space by the action of lytic transglycosylases. The product of this reaction, beta-D-N-acetylglucosamine-(1 -> 44)-1,6-anhydro-beta-D-N-acetylmuramyl-L-Ala-gamma-D-Glu-meso-DAP-D-Ala-D-Ala (compound 1), is internalized to begin the recycling events within the cytoplasm. The first step in the cytoplasmic recycling is catalyzed by the NagZ glycosylase, which cleaves in a hydrolytic reaction the N-acetylglucosamine glycosidic bond of metabolite 1. The reactions catalyzed by both the lytic glycosylases and NagZ are believed to involve oxocarbenium transition species. We describe herein the synthesis and evaluation of four iminosaccharides as possible mimetics of the oxocarbenium species, and we disclose one as a potent (compound 3, K-i = 300 +/- 15 nM) competitive inhibitor of NagZ.

  DOI：

  10.1021/ml2002746
• 作为产物：
  描述：

  D-谷氨酸 、 对甲苯磺酸 、 苯甲醇 以 甲苯 为溶剂， 生成 D-谷氨酸双苄酯对甲苯磺酸盐
  参考文献：
  名称：

  Synthesis and Structure Reassignment of Malylglutamate, a Recently Discovered Earthworm Metabolite

  摘要：

  Malylglutamate, a newly identified metabolite in earthworms, was synthesized using a traditional peptide coupling approach for assembling the amide from protected malate and glutamate precursors. The proposed structure (1) and a diastereomer were synthesized, but their NMR spectra did not match the natural sample. Further analysis of the natural sample using HMBC spectroscopy suggested an alternative attachment of the malyl moiety, and beta-malylglutamate (2) diastereomers were synthesized, L,L-2 and D,D-2. NMR spectra were an excellent match with the natural sample, and chiral-phase chromatography was employed to identify (-)-beta-L-malyl-L-glutamate (2) as the isomer native to Eisenia fetida.

  DOI：

  10.1021/acs.jnatprod.8b01083

文献信息

• 屏蔽剂及其用途
  申请人：恩多塞特公司

  公开号：CN113166087A

  公开（公告）日：2021-07-23

  本公开内容涉及可用作用于PSMA疗法的屏蔽剂的化合物。本公开内容涉及用与一种或多种屏蔽剂组合的一种或多种放射治疗剂来治疗表达PSMA的癌症的方法。本公开内容涉及使用与一种或多种屏蔽剂组合的含有放射性核素的一种或多种显像剂的成像方法。本公开内容还涉及制备屏蔽剂的方法。
• Host Marking Pheromone (HMP) in the Mexican Fruit Fly Anastrepha ludens
  作者：Andrew J. F. Edmunds、Martin Aluja、Fransico Diaz-Fleischer、Bruno Patrian、Leonhard Hagmann

  DOI：10.2533/chimia.2010.37

  日期：——

  Host marking pheromones (HMPs) are used by insects to mark hosts (usually a fruit) where they have already laid eggs. The compounds serve as a deterrent to conspecifics avoiding over-infestation of hosts (i.e. repeated egg-laying into an already occupied/used host). If these HMPs are sprayed onto commercially valuable fruit they act as deterrents preventing attack by females interested in laying eggs into the valuable commodity. Having no insecticidal or toxic properties, and being natural products (or close derivatives thereof) they could be used as fruit sprays to replace insecticides, or in combination with other products to improve efficacy. This review discusses the isolation, and synthesis of the HMP of the Mexican fruit fly Anastrepha ludens a feared pest of citrus and mangos in Mexico and Central America. This compound is also recognized by females of other pestiferous species in the same genus Anastrepha distributed from the Southern USA to Northern Argentina, including many Caribbean Islands. The synthetic HMP was shown to exhibit strong electrophysiological activity against A. ludens and excellent interspecies cross recognition with other Anastrepha species. Behavioural tests confirmed the HMP deterring effect of the synthetic natural product. Further studies enabled us to drastically simplify the structure of the HMP and obtain a derivative, which we named Anastrephamide, which shows HMP deterring effects very similar to the natural product in laboratory and field tests. The potential use of such HMP derivatives in a crop protection scenario is briefly discussed.

  寄主标记信息素（HMPs）被昆虫用来标记寄主（通常是水果），表明它们已经在那里产卵。这些化合物作为一种抑制剂，避免同类过度寄生寄主（即重复在已被占用/使用的寄主中产卵）。如果将这些HMP喷洒到商业有价值的水果上，它们将起到抑制作用，防止雌性昆虫对有价值的商品产卵攻击。由于没有杀虫或毒性，且为天然产品（或其近似衍生物），它们可以用作水果喷雾剂，以取代杀虫剂，或与其他产品结合以提高效果。这篇评论讨论了墨西哥果蝇Anastrepha ludens的HMP的分离和合成，这是墨西哥和中美洲柑橘和芒果的可怕害虫。这种化合物也被同属Anastrepha的其他害虫物种的雌性识别，这些物种分布在从美国南部到阿根廷北部，包括许多加勒比岛屿。合成的HMP表现出对A. ludens的强电生理活性，与其他Anastrepha物种具有出色的种间交叉识别能力。行为测试证实了合成天然产品的HMP抑制效果。进一步的研究使我们大大简化了HMP的结构，并获得了一个衍生物，我们将其命名为Anastrephamide，它在实验室和田间试验中显示出与天然产品非常相似的HMP抑制效果。这种HMP衍生物在作物保护方案中的潜在用途被简要讨论。
• Glycosyl-Substituted Dicarboxylates as Detergents for the Extraction, Overstabilization, and Crystallization of Membrane Proteins
  作者：Kim-Anh Nguyen、Marine Peuchmaur、Sandrine Magnard、Romain Haudecoeur、Cédric Boyère、Saravanan Mounien、Ikram Benammar、Veronica Zampieri、Sébastien Igonet、Vincent Chaptal、Anass Jawhari、Ahcène Boumendjel、Pierre Falson

  DOI：10.1002/anie.201713395

  日期：2018.3.5

  To tackle the problems associated with membrane protein (MP) instability in detergent solutions, we designed a series of glycosyl‐substituted dicarboxylate detergents (DCODs) in which we optimized the polar head to clamp the membrane domain by including, on one side, two carboxyl groups that form salt bridges with basic residues abundant at the membrane–cytoplasm interface of MPs and, on the other

  为了解决清洁剂溶液中与膜蛋白（MP）不稳定性相关的问题，我们设计了一系列糖基取代的二羧酸盐清洁剂（DCOD），其中我们优化了极性头，通过在一侧包含两个羧基来夹持膜结构域。形成盐桥的基团具有大量残留在MPs的膜-细胞质界面上的碱性残基，另一方面是形成氢键的糖。经萃取，将DCODs图8b，图8c和9b中保存BMRA，一个ATP结合盒泵的ATP酶的功能，更有效地比参考或最近设计的洗涤剂。所述DCODs 8，图8b，图8f，9，和9 b引起BmrA的热位移为20至29°C，天然形式的G蛋白偶联腺苷受体A 2A R的热位移为13至21°C 。化合物8 f和8 g改善了BmrA晶体的衍射分辨率从6到4Å。因此，DCOD被认为是MP的结构生物学的有前途和强大的工具。
• Synthesis of New Lipophilic Phosphonate and Phosphonamidate Analogues of N-Acetylmuramyl-L-alanyl-D-isoglutamine Related to LK 423
  作者：Stanislav Gobec、Uroš Urleb

  DOI：10.3390/70400394

  日期：——

  A syntheses of three new muramyl dipeptide (MDP) analogues related to LK 423 as potential immunomodulators are presented. The dipeptide part of the lead compound was modified by introducing a phosphonamide isostere instead of the amide bond between Lalanine and D-glutamic acid (or D-isoglutamine), yielding new MDP analogues 5 and 9. Furthermore, the amide bond between L-Ala and D-Glu was replaced by a phosphonate isostere, giving peptidyl phosphonate 14. The scope and limitations of the synthetic strategies employed are discussed.

  本文介绍了三种与LK 423相关的新型肽聚糖二肽（MDP）类似物，作为潜在的免疫调节剂。通过用磷酰胺异构体替代L-丙氨酸和D-谷氨酸（或D-异谷氨酸）之间的酰胺键，修改了主要化合物的二肽部分，得到新的MDP类似物5和9。此外，L-丙氨酸和D-谷氨酸之间的酰胺键被磷酸酯异构体替代，生成了肽磷酸酯14。讨论了所采用合成策略的范围和局限性。
• Large-scale synthesis of anticoagulant decapeptide MDL 28050
  作者：William J. Hoekstra、Shyam S. Sunder、Robert J. Cregge、Louis A. Ashton、Kenneth T. Stewart、Chi-Hsin R. King

  DOI：10.1016/s0040-4020(01)88142-4

  日期：——

  A solution phase synthesis of the anticoagulant decapeptide Suc-Tyr-Glu-Pro-Ile-Pro-Glu-Glu-Ala-Cha-D-Glu-OH (, MDL 28050) on a large scale is described. Our strategy employed in the 24-step total synthesis relies on a convergent approach. The basic feature is the preparation and the coupling of two protected pentapeptides, 2 and 3. Several key intermediates were purified by crystallizations including

  描述了大规模的抗凝血十肽Suc-Tyr-Glu-Pro-Ile-Pro-Glu-Glu-Ala-Cha- D -Glu-OH的溶液相合成。我们在24步全合成中采用的策略依赖于收敛方法。基本特征是两个受保护的五肽2和3的制备和偶联。通过结晶纯化了几种关键中间体，包括保护的十肽21。仅需一次纯化即可进行制备型HPLC。使用这种合成路线，我们以40克的规模制备了98％的纯净最终产品1。该过程的总产率为约20％。