D-谷氨酸-5-甲酯 | 6461-04-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 天然氨基酸及其衍生物
• 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-5-甲酯
• 英文名称: D-glutamic acid γ-methyl ester
• 英文别名: (2R)-2-azaniumyl-5-methoxy-5-oxopentanoate
• CAS: 6461-04-7
• 化学式: C₆H₁₁NO₄
• mdl: MFCD00237069
• 分子量: 161.158
• InChiKey: ZGEYCCHDTIDZAE-SCSAIBSYSA-N

物化性质

• 熔点：
  175-176℃
• 沸点：
  316.1±37.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  -3.4
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  89.6
• 氢给体数：
  2
• 氢受体数：
  5

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: H-D-Glu(OMe)-OH
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: H-D-Glu(OMe)-OH
CAS number: 6461-04-7

---

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.

---

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.

---

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.

---

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:

---

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.

---

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: C6H11NO4
Molecular weight: 161.2

---

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.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

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

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  D-谷氨酸-5-甲酯 在 ammonium hydroxide 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 16.0h， 生成 Boc-D-isoGln-OMe
  参考文献：
  名称：

  具有增强佐剂活性的胞壁酰二肽类似物的合成

  摘要：

  N-Acetylmuramyl-L-alanyl-D-isoglutamine (MDP) 和十三个新的类似物是通过常规有机化学方法合成的，使用二环己基碳二亚胺-N-羟基-5-降冰片烯-2,3-二甲酰亚胺作为偶联剂。测定了它们在豚鼠中诱导对 N-乙酰基-3-(4-arsonophenylazo)-L-酪氨酸的迟发型超敏反应的能力。结果表明，与 MDP 中乳酸部分相邻的 α-氨基酸的存在对于高生物活性很重要，缬氨酸类似物具有最有利的作用。讨论了构效关系。

  DOI：

  10.1246/bcsj.53.2570
• 作为产物：
  描述：

  L-谷氨酸-5-甲酯 以 水 为溶剂， 生成 D-谷氨酸-5-甲酯
  参考文献：
  名称：

  Effect of the side chain on the racemization of amino acids in aqueous solution

  摘要：

  DOI：

  10.1021/jo00280a017

文献信息

• Synthesis and Biological Activities of New 2-Substituted 1,4-Benzoxazine Derivatives.
  作者：Masahiro KAJINO、Yumiko SHIBOUTA、Kohei NISHIKAWA、Kanji MEGURO

  DOI：10.1248/cpb.39.2896

  日期：——

  A series of new 1, 4-benzoxazine derivatives (XI, XII) possessing (4-phenyl-1-piperazinyl)alkyl moieties at the 2-position and related compounds (XIII) were synthesized and tested for calcium antagonistic, calmodulin antagonistic and antihypertensive activities. Various compounds had in vitro calmodulin antagonistic activity superior or comparable to that of trifluoperazine. Among these compounds, tetrahydronaphtho[2, 3-b][1, 4]oxazine derivatives such as 51, 53, 54, 58, 59, 60, 73 and 75 showed potent antihypertensive effects in spontaneously hypertensive rats. Optical isomers of 51 were also synthesized and evaluated biologically. No differences in biological activities were seen between the enantiomers.

  一系列新的1,4-苯并恶嗪衍生物（XI，XII）在2位具有（4-苯基-1-哌嗪基）烷基部分及相关化合物（XIII）被合成并测试了钙拮抗、钙调素拮抗和降压活性。多种化合物在体外表现出优于或相当于三氟拉嗪的钙调素拮抗活性。其中，四氢萘并[2,3-b][1,4]恶嗪衍生物如51、53、54、58、59、60、73和75在自发性高血压大鼠中显示出强大的降压效果。51的光学异构体也被合成并进行了生物学评估。这些光学异构体之间在生物活性上没有差异。
• Synthesis of Carbapenems Containing Peptidoglycan Mimetics and Inhibition of the Cross‐Linking Activity of a Transpeptidase of <scp>l,d</scp> Specificity
  作者：Saidbakhrom Saidjalolov、Zainab Edoo、Matthieu Fonvielle、Louis Mayer、Laura Iannazzo、Michel Arthur、Mélanie Etheve‐Quelquejeu、Emmanuelle Braud

  DOI：10.1002/chem.202004831

  日期：2021.2.15

  The carbapenem class of β‐lactams has been optimized against Gram‐negative bacteria producing extended‐spectrum β‐lactamases by introducing substituents at position C2. Carbapenems are currently investigated for the treatment of tuberculosis as these drugs are potent covalent inhibitors of l,d‐transpeptidases involved in mycobacterial cell wall assembly. The optimization of carbapenems for inactivation

  碳青霉烯类β-内酰胺类通过针对C2位置引入取代基而针对产生广谱β-内酰胺酶的革兰氏阴性细菌进行了优化。目前正在研究碳青霉烯类药物用于治疗结核病，因为这些药物是l，d的有效共价抑制剂参与分枝杆菌细胞壁组装的转肽酶。本文通过利用C 8羟基的亲核性引入化学多样性来寻找用于灭活这些异常靶标的碳青霉烯类的优化。由于β-内酰胺是肽聚糖前体的结构类似物，因此选择取代基可增加药物和底物之间的相似性。有效地合成了十四个肽-卡宾。由于在位置C2引入苯乙硫基取代基的积极影响，它们比美罗培南参考药物更有效，但在位置C8添加的拟肽不能进一步提高活性。因此，可以修饰位置C8以调节高效碳青霉烯类的药代动力学性质。
• Design and synthesis of novel metalloproteinase inhibitors
  作者：Shingo Nakatani、Masahiro Ikura、Shingo Yamamoto、Yoshitaka Nishita、Satoshi Itadani、Hiromu Habashita、Tsuneyuki Sugiura、Koji Ogawa、Hiroyuki Ohno、Kanji Takahashi、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmc.2006.03.032

  日期：2006.8

  L-glutamic acid derivatives. Among the compounds tested, N-[4-(benzofuran-2-yl)benzoyl] 4-amino-4S-hydroxymethylbutyric acid hydroxamates derived from L-glutamic acid demonstrated more potent inhibitory activity against MMP-2 and MMP-9 compared with the corresponding 2S-hydroxy analogs or 3S-hydroxy analogs, respectively, which were derived from (-)-malic acid. Structure-activity relationship study

  合成了一系列的N-苯甲酰基4-氨基丁酸异羟肟酸酯类似物，并将其评估为基质金属蛋白酶抑制剂。合成工作的重点是使用容易获得的起始原料对4-氨基丁酸部分进行化学修饰。这样，使用可商购的起始原料例如4-氨基丁酸，（+）-和（-）-苹果酸以及D-和L-谷氨酸衍生物进行化学修饰。在测试的化合物中，衍生自L-谷氨酸的N- [4-（苯并呋喃-2-基）苯甲酰基] 4-氨基-4S-羟甲基丁酸异羟肟酸酯与MMP-2和MMP-9相比，对MMP-2和MMP-9的抑制作用更强。分别衍生自（-）-苹果酸的相应2S-羟基类似物或3S-羟基类似物。提出了构效关系研究。
• [EN] COMPOUNDS AS TYROSINE KINASE MODULATORS<br/>[FR] COMPOSÉS À UTILISER EN TANT QUE MODULATEURS DES TYROSINE KINASES
  申请人：ALLERGAN INC

  公开号：WO2015069287A1

  公开（公告）日：2015-05-14

  The present invention is directed to novel compounds of Formula I. The compounds of the present invention are potent tyrosine kinase modulators, and are suitable for the treatment and prevention of diseases and conditions related to abnormal activities of tyrosine kinase receptors.

  本发明涉及公式I的新化合物。本发明的化合物是有效的酪氨酸激酶调节剂，适用于治疗和预防与酪氨酸激酶受体异常活动相关的疾病和症状。
• SHORT-ACTING BENZODIAZEPINE DERIVATIVES, PREPARATION METHOD THEREFOR, AND USE THEREOF
  申请人：SICHUAN KELUN-BIOTECH BIOPHARMACEUTICAL CO., LTD.

  公开号：US20180312511A1

  公开（公告）日：2018-11-01

  The present invention relates to a benzodiazepine derivative of Formula I as a short-acting anesthetic, a pharmaceutical composition comprising the same, a kit comprising the same, a preparation method thereof, an method of anesthesia using the same and use thereof in the manufacture of an anesthetic medicament.

  本发明涉及一种苯二氮䓬类衍生物，其化学式为I，作为一种短效麻醉剂，包括该衍生物的药物组合物，包括该衍生物的试剂盒，其制备方法，使用该衍生物的麻醉方法以及在制造麻醉药物中使用该衍生物的用途。