Cbz-D-焦谷氨酸 | 78339-57-8

• 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: Cbz-D-焦谷氨酸
• 英文名称: (R)-Cbz-glutamic acid
• 英文别名: Z-D-Pyr-OH；(2R)-5-oxo-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid
• CAS: 78339-57-8
• 化学式: C₁₃H₁₃NO₅
• mdl: MFCD00077036
• 分子量: 263.25
• InChiKey: VHSFUGXCSGOKJX-SNVBAGLBSA-N

物化性质

• 熔点：
  138-144℃
• 沸点：
  525.4±50.0 °C(Predicted)
• 密度：
  1.408±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933790090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Z-D-Pyr-oh
Synonyms:

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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: Z-D-Pyr-oh
CAS number: 78339-57-8

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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: C13H13NO5
Molecular weight: 263.2

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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.

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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：

  Cbz-D-焦谷氨酸 在 二苯基膦叠氮化物 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (R)-2-Isocyanato-5-oxo-pyrrolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Synthesis of Optically Pure 5-Aminopyrrolidin-2-one Formic Acid Salt: A Key Intermediate for the Incorporation of the Pyroglutamyl Geminal Diamino Analogue intoRetro-InversoPeptides

  摘要：

  DOI：

  10.1055/s-1985-31183

文献信息

• THERAPEUTIC AGENT FOR DIABETES
  申请人：Japan Tobacco Inc.

  公开号：EP0885869A1

  公开（公告）日：1998-12-23

  A therapeutic agent for diabetes, which comprises a compound of the formula [I] wherein Xis a group of the formula wherein R4 and R5 are the same or different and each is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, and R6 is a hydrogen atom or an amino-protecting group; R1 is an optionally substituted alkyl having 1 to 5 carbon atoms, an optionally substituted alkenyl having 2 to 6 carbon atoms and the like, R2 is a hydrogen atom, an optionally substituted alkyl having 1 to 5 carbon atoms and the like, R2' is a hydrogen atom, and R3 is an optionally substituted alkyl having 1 to 5 carbon atoms and the like, a prodrug thereof, a pharmaceutically acceptable salt thereof, a hydrate thereof and a solvate thereof. The compound of the present invention shows superior blood sugar decreasing action on the state of hyperglycemia, but does not affect the blood sugar when it is in the normal range or in the hypoglycemic state, which means that it is free of serious side effects such as hypoglycemia. Therefore, the compound of the present invention is useful as a therapeutic drug for diabetes and also useful as a preventive of the chronic complications of diabetes.

  用于治疗糖尿病的疗法剂，包括公式[I]的化合物 其中 X是公式的组 其中R4和R5相同或不同，每个都是氢原子，可选地取代的具有1至5个碳原子的烷基等等，R6是氢原子或氨基保护基团；R1是具有1至5个碳原子的可选取代烷基，具有2至6个碳原子的可选取代烯基等等，R2是氢原子，具有1至5个碳原子的可选取代烷基等等，R2'是氢原子，R3是具有1至5个碳原子的可选取代烷基等等，其前药，药用可接受盐，水合物和溶剂化物。 本发明的化合物在血糖升高状态下表现出优越的降血糖作用，但在正常范围或低血糖状态下不影响血糖，这意味着它没有低血糖等严重副作用。因此，本发明的化合物作为治疗糖尿病的药物很有用，也用作预防糖尿病慢性并发症。
• Dipeptidyl peptidase-IV inhibitors
  申请人：Hulin Bernard

  公开号：US20050234065A1

  公开（公告）日：2005-10-20

  The invention provides compounds of Formula (I) or prodrugs thereof, or pharmaceutically acceptable salts of said compounds or prodrugs, or solvates of said compounds, prodrugs or salts, wherein A, N, X and R 1 are as defined herein; pharmaceutical compositions thereof; and methods of using the pharmaceutical compositions for the treatment of diseases, including Type 2 diabetes, Type 1 diabetes, impaired glucose tolerance, hyperglycemia, metabolic syndrome (syndrome X and/or insulin resistance syndrome), glucosuria, metabolic acidosis, arthritis, cataracts, diabetic neuropathy, diabetic nephropathy, diabetic retinopathy, diabetic cardiomyopathy, obesity, conditions exacerbated by obesity, hypertension, hyperlipidemia, atherosclerosis, osteoporosis, osteopenia, frailty, bone loss, bone fracture, acute coronary syndrome, short stature due to growth hormone deficiency, infertility due to polycystic ovary syndrome, anxiety, depression, insomnia, chronic fatigue, epilepsy, eating disorders, chronic pain, alcohol addiction, diseases associated with intestinal motility, ulcers, irritable bowel syndrome, inflammatory bowel syndrome; short bowel syndrome; and the prevention of disease progression in Type 2 diabetes.

  该发明提供了Formula (I)的化合物或其前药，或者该化合物或前药的药用可接受盐，或者该化合物、前药或盐的溶剂化合物，其中A、N、X和R1如本文所定义；以及这些药物组合物；以及使用这些药物组合物治疗疾病的方法，包括2型糖尿病、1型糖尿病、糖耐量受损、高血糖、代谢综合征（综合征X和/或胰岛素抵抗综合征）、葡萄糖尿病、代谢性酸中毒、关节炎、白内障、糖尿病神经病、糖尿病肾病、糖尿病视网膜病、糖尿病心肌病、肥胖、由肥胖恶化的疾病、高血压、高脂血症、动脉粥样硬化、骨质疏松症、脆弱、骨质流失、骨折、急性冠状动脉综合征、生长激素缺乏引起的矮小症、多囊卵巢综合征引起的不孕症、焦虑、抑郁、失眠、慢性疲劳、癫痫、进食障碍、慢性疼痛、酒精成瘾、与肠道蠕动相关的疾病、溃疡、肠易激综合征、炎症性肠病；短肠综合征；以及预防2型糖尿病疾病进展。
• ADENINE DERIVATIVES
  申请人：Buchstaller Hans-Peter

  公开号：US20100160352A1

  公开（公告）日：2010-06-24

  Novel adenine derivatives of the formula (I), in which R 1 , R 2 , R 3 , X and Y have the meanings indicated in Claim 1 , are HSP90 inhibitors and can be used for the preparation of a medicament for the treatment of diseases in which the inhibition, regulation and/or modulation of HSP90 plays a role.

  新型腺嘌呤衍生物的化学式（I），其中R1、R2、R3、X和Y具有权利要求1中指示的含义，是HSP90抑制剂，可用于制备用于治疗需要HSP90抑制、调节和/或调控的疾病的药物。
• Stereospecific Palladium-Catalyzed C–H Arylation of Pyroglutamic Acid Derivatives at the C3 Position Enabled by 8-Aminoquinoline as a Directing Group
  作者：Oscar Verho、Micah Maetani、Bruno Melillo、Jochen Zoller、Stuart L. Schreiber

  DOI：10.1021/acs.orglett.7b01776

  日期：2017.9.1

  Pd-catalyzed protocol for the C–H arylation of pyroglutamic acid derivatives that uses 8-aminoquinoline as a directing group is described. The reaction was shown to proceed efficiently with a variety of aryl and heteroaryl iodides bearing different functional groups, giving C3-arylated cis products in good to high yields. Removal of the 8-aminoquinoline unit from these C–H arylation products enables access to

  描述了一种高效且立体定向的钯催化焦谷氨酸衍生物的CH芳基化反应的方案，该方案使用8-氨基喹啉作为导向基团。已表明，使用带有不同官能团的各种芳基和杂芳基碘化物可以有效地进行反应，从而以高至高收率得到C3芳基化的顺式产物。从这些C–H芳基化产物中除去8-氨基喹啉单元可以使用合成上有用的基于顺式和反式焦谷氨酸的结构单元。
• Isolation, Synthesis, and Radical-Scavenging Activity of Rhodomelin A, a Ureidobromophenol from the Marine Red Alga <i>Rhodomela confervoides</i>
  作者：Ke Li、Ya-Fei Wang、Xiao-Ming Li、Wei-Jia Wang、Xu-Ze Ai、Xin Li、Sui-Qun Yang、James B. Gloer、Bin-Gui Wang、Tao Xu

  DOI：10.1021/acs.orglett.7b03716

  日期：2018.1.19

  from Rhodomela confervoides. Its structure was elucidated by spectroscopic analysis. Both enantiomers of 1 were synthesized using a convergent strategy starting from d/l-pyroglutamic acids, respectively, allowing assignment of the R-configuration for the naturally occurring isomer by chiral HPLC analysis. Rhodomelin A represents the first example of a naturally occurring ureidopyrrolidone alkaloid incorporating

  一种新型的脲基溴酚，红景天蛋白A（1），从红景天中得到了表征。通过光谱分析阐明了其结构。1的两个对映异构体分别使用收敛策略从d / l-焦谷氨酸开始合成，并通过手性HPLC分析确定了天然异构体的R-构型。杜鹃花蛋白A代表掺入γ-氨基丁酸单元的天然脲基吡咯烷酮生物碱的第一个实例。测定了1对DPPH（1，1-二苯基-2-吡啶并肼基）和ABTS（2，2′-叠氮基双（3-乙基苯并噻唑啉-6-磺酸根））的清除活性。