N-α-棕榈酰-S-[2,3-双(棕榈酰氧基)-(2RS)-丙基]-L-半胱氨酸 | 87420-41-5

• 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-α-棕榈酰-S-[2,3-双(棕榈酰氧基)-(2RS)-丙基]-L-半胱氨酸
• 中文别名: 棕榈酰-Cys((RS)-2,3-二(棕榈酰氧基)-丙基)-OH
• 英文名称: Pam3Cys
• 英文别名: (2R)-3-(2,3-bis(palmitoyloxy)propylthio)-2-palmitamidopropanoic acid；Pam3Cys-OH；N-Palmitoyl-2,3-bis(palmitoyloxy)-2-propylcysteine；(2R)-3-[2,3-di(hexadecanoyloxy)propylsulfanyl]-2-(hexadecanoylamino)propanoic acid
• CAS: 87420-41-5
• 化学式: C₅₄H₁₀₃NO₇S
• 分子量: 910.48
• InChiKey: PZFZLRNAOHUQPH-GOOVXGPGSA-N

物化性质

• 沸点：
  907.8±65.0 °C(Predicted)
• 密度：
  0.966±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  21.6
• 重原子数：
  63
• 可旋转键数：
  53
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  144
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• WGK Germany：
  3

SDS

---

Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Pam3-Cys-OH
CAS-No. : 87420-41-5
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

---

Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No 1272/2008
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
Caution - substance not yet tested completely.
Other hazards - none

---

Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
: N-α-Palmitoyl-S-[2,3-bis(palmitoyloxy)-(2RS)-propyl]-L-cysteine
Synonyms
Palmitoyl-Cys((RS)-2,3-di(palmitoyloxy)-propyl)-OH
Formula : C54H103NO7S
Molecular Weight : 910,46 g/mol

---

Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
Indication of any immediate medical attention and special treatment needed
no data available

---

Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx), Sulphur oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

---

Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.

---

Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.Normal measures for preventive fire
protection.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Store under inert gas. Air sensitive.
Specific end uses
no data available

---

Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).

---

Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: powder
Colour: white
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

---

Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

---

Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Additional Information
RTECS: Not available

---

Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

---

Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.

---

Section 14. TRANSPORT INFORMATION
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

---

---

SECTION 15 - REGULATORY INFORMATION
N/A

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  H-Asn-Ser(Bu^t)-Gly-Gly-Ser(Bu^t)-OBu^t 、 N-α-棕榈酰-S-[2,3-双(棕榈酰氧基)-(2RS)-丙基]-L-半胱氨酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 生成 S-<(2RS)-2,3-Bis(palmitoyloxy)propyl>-N^α-palmitoyl-Cys-Asn-Ser(Bu^t)-Gly-Gly-Ser(Bu^t)-OBu^t
  参考文献：
  名称：

  具有微生物来源的免疫活性脂肽WS1279的结构和合成。

  摘要：

  WS1279的结构，分离自链霉菌。作为免疫活性脂肽，已经根据化学和物理证据推导为S- [2,3-双（棕榈酰氧基）丙基] -Nα-棕榈酰-Cys-Asn-Ser-Gly-Gly-Ser-OH。通过合成证实了这一点。

  DOI：

  10.1248/cpb.39.607
• 作为产物：
  描述：

  (2R)-3-(3-(allyloxy)-2-(tert-butoxycarbonylamino)-3-oxopropylthio)propane-1,2-diyl dipalmitate 在 四(三苯基膦)钯 、 HATU 、 N,N-二异丙基乙胺 、 N-甲基苯胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-α-棕榈酰-S-[2,3-双(棕榈酰氧基)-(2RS)-丙基]-L-半胱氨酸
  参考文献：
  名称：

  Conjugated TLR7 and/or TLR8 and TLR2 polycationic agonists

  摘要：

  公开号：

  EP2769738B1

文献信息

• MULTI-VALENT ADJUVANT DISPLAY
  申请人：Psioxus Therapeutics Limited

  公开号：US20170112923A1

  公开（公告）日：2017-04-27

  The present invention provides an adjuvant-polymer construct comprising a polymer backbone which is covalently linked to 3 or more adjuvants, wherein the 3 or more adjuvants are each present in a pendant side chain, the adjuvants being connected to the polymer backbone either directly or via a spacer group.

  本发明提供了一种佐剂-聚合物构造体，包括一个聚合物骨架，该聚合物骨架与3个或更多佐剂共价连接，其中这3个或更多佐剂分别存在于一个挂链侧链中，佐剂与聚合物骨架之间通过直接连接或通过间隔基团连接。
• CONJUGATED TLR7 AND/OR TLR8 AND TLR2 AGONISTS
  申请人：CAYLA

  公开号：US20140141033A1

  公开（公告）日：2014-05-22

  A conjugated compound of formula Q-Z—R 4 wherein Q is a TLR7 and/or TLR8 agonist and Z—R 4 is a TLR2 agonist, and the uses thereof in the treatment of infection, cancer or immune disorders or for use in vaccines.

  一种配方为Q-Z—R4的共轭化合物，其中Q是TLR7和/或TLR8激动剂，Z—R4是TLR2激动剂，以及它们在治疗感染、癌症或免疫紊乱或用于疫苗中的用途。
• Solution and Solid-Support Synthesis of a Potential Leishmaniasis Carbohydrate Vaccine
  作者：Michael C. Hewitt、Peter H. Seeberger

  DOI：10.1021/jo015521z

  日期：2001.6.1

  The synthesis of a potential carbohydrate vaccine for the parasitic disease leishmaniasis is described. New solution- and solid-phase synthetic strategies were explored for the assembly of a unique tetrasaccharide antigen found on the Leishmania lipophosphoglycan. An initial solution-phase synthesis relied on thioglycosides as building blocks and the establishment of the central disaccharide from lactal

  描述了用于寄生虫利什曼病的潜在碳水化合物疫苗的合成。探索了新的溶液和固相合成策略，用于组装在利什曼原虫脂磷酸聚糖上发现的独特的四糖抗原。最初的溶液相合成依赖于硫糖苷作为结构单元，并通过氧化还原序列从乳清中建立了中心二糖。在解决方案和固体支持上都完成了第二种方法。固相合成依赖于单糖单元的组装，并用于评估有效安装半乳糖β-（1-4）甘露糖苷中的不同糖基化剂。事实证明，糖基磷酸酯最成功。利什曼原虫菌盖的第一次固相合成提供了以18％的总收率快速获得四糖的途径，而仅需一个纯化步骤。将合成的帽四糖与免疫刺激剂Pam3Cys结合以生成完全合成的碳水化合物疫苗1，并与载体蛋白KLH结合以形成半合成疫苗2。目前，这两种构建体均已在小鼠体内进行了初步免疫学实验，旨在开发针对寄生虫的疫苗疾病利什曼病。
• [EN] CANCER IMMUNOTHERAPY<br/>[FR] IMMUNOTHÉRAPIE ANTICANCÉREUSE
  申请人：ENA THERAPEUTICS PTY LTD

  公开号：WO2021042171A1

  公开（公告）日：2021-03-11

  Methods, compounds, compositions and kits for the treatment and/or prevention of cancer are provided. In particular, methods for the treatment of cancer comprising the administration of a TLR2 agonist, such as a conjugate of dipalmitoyl-S-glyceryl-cysteine (Pam2Cys) and polyethylene glycol (PEG), more particularly a Pam2Cys-Ser-PEG compound, and an immunostimulant such as an anti-PD-1, anti-PDL-1, anti-PL- 1, or anti-CTLA-4 immunotherapeutic, are provided.

  提供了治疗和/或预防癌症的方法、化合物、组合物和工具包。特别地，提供了治疗癌症的方法，包括给予TLR2激动剂，例如二棕榈酰-S-甘油半胱氨酸（Pam2Cys）和聚乙二醇（PEG）的共轭物，更具体地说是Pam2Cys-Ser-PEG化合物，以及免疫刺激剂，例如抗PD-1、抗PDL-1、抗PL-1或抗CTLA-4免疫治疗剂。
• Adjuvanting Material
  申请人：Jackson David C.

  公开号：US20080233143A1

  公开（公告）日：2008-09-25

  The present invention provides an adjuvanting material, the adjuvanting material comprising a lipid dendritic cell targeting moiety to which is covalently linked a metal chelating group. Further, the present invention provides an immunogenic composition comprising (a) a lipid dendritic cell targeting moiety to which is covalently linked a metal chelating group; (b) an antigen comprising a metal affinity tag; and optionally (c) metal ions, whereby the antigen is linked to the lipid dendritic cell targeting moiety via the interaction between the metal affinity tag and the metal chelating group.

  本发明提供了一种辅助材料，该辅助材料包括一个脂质树突状细胞靶向基团，其中与之共价结合的是一个金属螯合基团。此外，本发明还提供了一种免疫原组合物，包括（a）一个脂质树突状细胞靶向基团，其中与之共价结合的是一个金属螯合基团；（b）一个包含金属亲和标签的抗原；以及可选的（c）金属离子，因此抗原通过金属亲和标签和金属螯合基团之间的相互作用与脂质树突状细胞靶向基团连接。