N-叔丁氧羰基-D-异谷氨酰胺 | 55297-72-8

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 谷氨酰胺类衍生物
• 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: N-叔丁氧羰基-D-异谷氨酰胺
• 中文别名: Boc-D-异谷氨酰胺
• 英文名称: (R)-5-amino-4-((tert-butoxycarbonyl)amino)-5-oxopentanoic acid
• 英文别名: Boc-D-γ-Glu-NH2；Boc-D-isoGln-OH；BOC-D-isoGln；Boc-D-Glu-NH2；(4R)-5-amino-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-oxopentanoic acid
• CAS: 55297-72-8
• 化学式: C₁₀H₁₈N₂O₅
• mdl: MFCD00056702
• 分子量: 246.263
• InChiKey: GMZBDBBBJXGPIH-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  119
• 氢给体数：
  3
• 氢受体数：
  5

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: Boc-d-glu-nh2
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: Boc-d-glu-nh2
CAS number: 55297-72-8

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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: C10H18N2O5
Molecular weight: 246.3

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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：

  N-叔丁氧羰基-D-异谷氨酰胺 在 2,2,6,6-四甲基哌啶 、 N-羟基-7-氮杂苯并三氮唑 、 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 L-alanyl-D-isoglutamine benzyl ester trifluoroacetate
  参考文献：
  名称：

  Convergent Synthesis of Novel Muramyl Dipeptide Analogues: Inhibition of Porphyromonas gingivalis-Induced Pro-inflammatory Effects by High Doses of Muramyl Dipeptide

  摘要：

  Porphyromonas gingivalis (P.g.)-induced TNF-alpha can be affected by muramyl dipeptide (MDP) in a biphasic concentration-dependent manner. We found that in P.g.-exposed macrophages, treatment with 10 mu g/mL of MDP (MDP-low) up-regulated TNF-alpha by 29%, while 100 mu g/mL or higher (MDP-high) significantly decreased it (16% to 38%). MDP-high was found to affect the ubiquitin-editing enzyme A20 and activator protein 1 (AP1). An AP1 binding site was found in the promoter region of A20. A20 promoter activity was up-regulated after transfection of AP1 cDNA in cells. Four analogues of MDP (3-6) were prepared through a convergent strategy involving the synthesis of two unique carbohydrate fragments, 7a and 7b, using the peptide coupling reagents, EDCI and HOAt. Analogue 4 improved MDP function and P.g.-induced activities. We propose a new signaling pathway for TNF-alpha induction activated after exposing macrophages to both P.g. and MDP-high or analogue 4.

  DOI：

  10.1021/acs.jmedchem.6b00681
• 作为产物：
  描述：

  N-叔丁氧羰基-D-谷氨酸 1-甲酯 在 氨 作用下， 以 甲醇 为溶剂， 生成 N-叔丁氧羰基-D-异谷氨酰胺
  参考文献：
  名称：

  Arendt,A. et al., Roczniki Chemii, 1974, vol. 48, p. 1921 - 1927

  摘要：

  DOI：

文献信息

• Solid-phase synthesis of muramyl dipeptide (mdp) derivatives using a multipin method
  作者：Gang Liu、Shuo-De Zhang、Shu-Quan Xia、Zhen-Kai Ding

  DOI：10.1016/s0960-894x(00)00241-9

  日期：2000.6

  Solid-phase synthetic method of muramyl dipeptide derivatives is reported. A diverse library of muramyl dipeptides could be potentially synthesized by acylation, reductive alkylation, sulfonamide formation, urea formation, N-alkylation, amine addition, or component Ugi reactions based on this method for drug screening.

  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。
• Insights into the Mechanism of Action of the Two-Peptide Lantibiotic Lacticin 3147
  作者：Alireza Bakhtiary、Stephen A. Cochrane、Pascal Mercier、Ryan T. McKay、Mark Miskolzie、Clarissa S. Sit、John C. Vederas

  DOI：10.1021/jacs.7b04728

  日期：2017.12.13

  LtnA2) that displays nanomolar activity against many Gram-positive bacteria. Lacticin 3147 may exert its antimicrobial effect by several mechanisms. Isothermal titration calorimetry experiments show that only LtnA1 binds to the peptidoglycan precursor lipid II, which could inhibit peptidoglycan biosynthesis. An experimentally supported model of the resulting complex suggests that the key binding partners

  Lacticin 3147 是一种双肽 lantibiotc（LtnA1 和 LtnA2），对许多革兰氏阳性菌显示出纳摩尔级的活性。Lacticin 3147 可能通过多种机制发挥其抗菌作用。等温滴定量热实验表明，只有 LtnA1 与肽聚糖前体脂质 II 结合，可以抑制肽聚糖的生物合成。所得复合物的实验支持模型表明，关键的结合伙伴是 LtnA1 的 C 端和脂质 II 的焦磷酸盐。体内和体外检测的组合表明 LtnA1 和 LtnA2 可以诱导快速膜裂解，而无需脂质 II 结合。然而，脂质 II 的存在大大增加了乳酸菌素 3147 的活性。此外，
• Zaoral, Milan; Jezek, Jan; Krchnak, Viktor, Collection of Czechoslovak Chemical Communications, 1980, vol. 45, # 5, p. 1424 - 1446
  作者：Zaoral, Milan、Jezek, Jan、Krchnak, Viktor、Straka, Radovan

  DOI：——

  日期：——
• Peptide immunostimulants
  申请人：PFIZER INC.

  公开号：EP0227306B1

  公开（公告）日：1989-09-13
• Lefrancier; Bricas, Bulletin de la Societe Chimique de France, 1969, vol. 10, p. 3561 - 3566
  作者：Lefrancier、Bricas

  DOI：——

  日期：——