D-谷氨酸的α-酰胺盐酸盐 | 19522-40-8

• 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-谷氨酸的α-酰胺盐酸盐
• 中文别名: D-谷氨酸的Alpha-氨酰胺盐酸盐
• 英文名称: D-α-glutamine
• 英文别名: D-isoglutamine；D-isoGln；D-Isoglutamin；(4R)-5-amino-4-azaniumyl-5-oxopentanoate
• CAS: 19522-40-8
• 化学式: C₅H₁₀N₂O₃
• 分子量: 146.146
• InChiKey: AEFLONBTGZFSGQ-GSVOUGTGSA-N

物化性质

• 沸点：
  423.1±40.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: D-Glutamic acid alpha-amide, HCl
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: D-Glutamic acid alpha-amide, HCl
CAS number: 19522-40-8

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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: C5H10N2O3.ClH
Molecular weight: 182.6

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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, hydrogen chloride.

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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-谷氨酸的α-酰胺盐酸盐 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 (2R)-2-[[(2S)-2-[[(2R)-2-[(2R,3S,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-phenylmethoxyoxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-N'-[(2S)-1-amino-6-[[2-[1-(4-chlorobenzoyl)-5-methoxyindol-3-yl]acetyl]amino]-1-oxohexan-2-yl]pentanediamide
  参考文献：
  名称：

  使用多销方法固相合成穆拉基二肽（MDP）衍生物。

  摘要：

  报道了固相合成穆拉基二肽衍生物的方法。基于此药物筛选方法，可以通过酰化，还原烷基化，磺酰胺形成，尿素形成，N-烷基化，胺加成或组分Ugi反应潜在地合成多样的穆拉基二肽文库。

  DOI：

  10.1016/s0960-894x(00)00241-9
• 作为产物：
  描述：

  D-谷氨酸 在 palladium on activated charcoal ammonium hydroxide 、 硫酸 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 D-谷氨酸的α-酰胺盐酸盐
  参考文献：
  名称：

  使用多销方法固相合成穆拉基二肽（MDP）衍生物。

  摘要：

  报道了固相合成穆拉基二肽衍生物的方法。基于此药物筛选方法，可以通过酰化，还原烷基化，磺酰胺形成，尿素形成，N-烷基化，胺加成或组分Ugi反应潜在地合成多样的穆拉基二肽文库。

  DOI：

  10.1016/s0960-894x(00)00241-9

文献信息

• Preparation of<i>N</i>-Acetylmuramyl-L-[U-¹⁴<i>C</i>]alanyl-D-isoglutamine<i>via</i>a Novel Synthetic Route
  作者：Shoichi Kusumoto、Kazuhiro Ikenaka、Tetsuo Shiba

  DOI：10.1246/bcsj.52.1177

  日期：1979.4

  anyl-D-isoglutamine, its labeled compound, i.e., N-acetylmuramyl-L-[U-14C]alanyl-D-isoglutamine was synthesized. For this purpose, an entirely novel synthetic route for the muramyl dipeptide was exploited using cold materials and applied to the preparation of the labeled compound. A convenient synthetic procedure of isoglutamine derivatives is also described.

  为研究免疫佐剂活性N-乙酰胞壁酰-L-丙氨酰-D-异谷氨酰胺的作用机制，合成了其标记化合物N-乙酰胞壁酰-L-[U-14C]丙氨酰-D-异谷氨酰胺。为此，使用冷材料开发了一种全新的胞壁酰二肽合成路线，并将其应用于标记化合物的制备。还描述了异谷氨酰胺衍生物的方便合成程序。
• Lefrancier; Bricas, Bulletin de la Societe Chimique de France, 1969, vol. 10, p. 3561 - 3566
  作者：Lefrancier、Bricas

  DOI：——

  日期：——
• Synthesis of D- and L-Thalidomide and Related Studies
  作者：Y.Fulmer Shealy、Clyde E. Opliger、John A. Montgomery

  DOI：10.1002/jps.2600570507

  日期：1968.5
• A Novel Immunostimulator, <i>N</i>²-[α-<i>O</i>-Benzyl-<i>N</i>-(acetylmuramyl)-<scp>l</scp>-alanyl-<scp>d</scp>- isoglutaminyl]-<i>N</i>⁶-<i>trans</i>-(<i>m</i>-nitrocinnamoyl)-<scp>l</scp>-lysine, and Its Adjuvancy on the Hepatitis B Surface Antigen
  作者：Hong-Zhen Yang、Song Xu、Xue-Yan Liao、Suo-De Zhang、Zheng-Lun Liang、Bai-He Liu、Jin-Ye Bai、Chao Jiang、Jian Ding、Gui-Fang Cheng、Gang Liu

  DOI：10.1021/jm0493313

  日期：2005.8.1

  N-2-[(alpha-O-Benzyl-N-(acetylmuramyl)-L-alanyl-D-isoglutaminyl)]-AT6-trans-(m-nitrocinnamoyl)-L-lysine (muramyl dipeptide C, or MDP-C) has been synthesized as a novel, nonspecific immunomodulator. The present study shows that MDP-C induces strong cytolytic activity by macrophages on P388 leukemia cells and cytotoxic activity by cytotoxic T lymphocytes (CTLs) on P815 mastocytoma cells. Our results also indicate that MDP-C is an effective stimulator for production of interleukin-2 and interleukin-12 by murine bone morrow derived dendritic cells (BMDCs) and production of interferon-gamma by CTLs. Additionally, MDP-C increases the expression levels of several surface molecules, including CD11c, MHC class I, and intercellular adhesion molecule-1 in BMDCs. Moreover, MDP-C remarkably enhances the immune system's responsiveness to hepatitis B surface antigen (HBsAg) in hepatitis B virus transgenic mice for both antibody production and specific HBsAg T-cell responses ex vivo. Our results indicate that MDP-C is an apyrogenic, nonallergenic, and low-toxicity immunostimulator with great potential for diagnostic, immunotherapeutic, and prophylactic applications in diseases such as hepatitis B and cancers.
• Synthesis of a biologically active fluorescent muramyl dipeptide congener
  作者：C. K. Hiebert、W. C. Kopp、H. B. Richerson、C. F. Barfknecht

  DOI：10.1021/jm00366a014

  日期：1983.12

  A fluorescent-labeled muramyl dipeptide (MDP) has been prepared to probe immunoadjuvant cellular interactions. N-Acetylmuramyl-L-alanyl-D-isoglutamine (1) was synthesized in improved yield and reacted with 2-(fluoresceinylamino)-4,6-dichloro-s-triazine (DTAF, 2) to give the fluorescent adduct DTAF-MDP (3), attached through the 6-position of the sugar moiety. Adjuvant activity was assessed by using two different in vitro assays, macrophage spreading, and inhibition of macrophage migration. Both assays indicated that the apparent adjuvant activity of 3 is comparable to that of 1.