-L-胱氨酰基二甘氨酸 | 7729-20-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 甘氨酸类衍生物
• 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: -L-胱氨酰基二甘氨酸
• 英文名称: L-Cystinyl-diglycin
• 英文别名: L-cystine-bis-glycine；2-[[(2R)-2-azaniumyl-3-[[(2R)-2-azaniumyl-3-(carboxylatomethylamino)-3-oxopropyl]disulfanyl]propanoyl]amino]acetate
• CAS: 7729-20-6
• 化学式: C₁₀H₁₈N₄O₆S₂
• 分子量: 354.408
• InChiKey: KDJVKDYFFTWHBO-WDSKDSINSA-N

物化性质

• 沸点：
  788.5±60.0 °C(Predicted)
• 密度：
  1.535±0.06 g/cm3(Predicted)
• 溶解度：
  PBS（pH 7.2）：1 mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  -7.6
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  235
• 氢给体数：
  6
• 氢受体数：
  10

安全信息

• 储存条件：
  -20°C

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Cys-Gly, oxidized
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 7729-20-6
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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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
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : Cys(Cys-Gly)-Gly
Formula : C10H18N4O6S2
Molecular Weight : 354,40 g/mol
CAS-No. : 7729-20-6
No components need to be disclosed according to the applicable regulations.

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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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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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

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
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.

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SECTION 7: Handling and storage
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: -20 °C
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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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).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
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) Evapouration 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) Auto-ignition 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

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
no data available
Hazardous decomposition products
In the event of fire: see section 5

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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 sensitisation
no data available
Germ cell mutagenicity
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
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: Not available

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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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.

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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

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SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Further information
Copyright 2013 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

2-((R)-2-氨基-3-(R-)

反应信息

• 作为反应物：
  描述：

  -L-胱氨酰基二甘氨酸 在 氨 、 sodium 作用下， 生成 S-benzyl-L-cysteinylglycine
  参考文献：
  名称：

  ProbeMatchDB—a web database for finding equivalent probes across microarray platforms and species

  摘要：

  摘要：ProbeMatchDB是一个基于网络的数据库，旨在促进对EST/cDNA序列或STS标记的搜索，这些序列或标记可用于代表不同微阵列平台和物种中相同基因。它可用于根据Affymetirx GeneChip®s的结果在Research Genetics序列验证的克隆集中查找等价的EST克隆。它还将有助于识别在不同微阵列平台上代表人类、小鼠和大鼠同源基因的探针。 可用性：该数据库可通过点击“查询ProbeMatchDB”链接访问http://brainarray.mhri.med.umich.edu/MARRAY/BC_ASP/brainarray.htm。 联系人：[e-mail]

  DOI：

  10.1093/bioinformatics/18.3.488
• 作为产物：
  描述：

  N,N'-二(苄氧羰基)-L-胱氨酸 在 1,4-二氧六环 、 barium dihydroxide 、 五氯化磷 作用下， 生成 -L-胱氨酰基二甘氨酸
  参考文献：
  名称：

  679.由脱水N-羧基氨基酸合成简单的肽

  摘要：

  DOI：

  10.1039/jr9500003461

文献信息

• A study of the glutathione metaboloma peptides by energy-resolved mass spectrometry as a tool to investigate into the interference of toxic heavy metals with their metabolic processes
  作者：Federico Maria Rubino、Marco Pitton、Gabri Brambilla、Antonio Colombi

  DOI：10.1002/jms.1143

  日期：2006.12

  from ions containing the gamma-glutamyl residue to yield a sulfenium cation was a much more energetic process than those not containing them, suggesting that the redox potential of the thiol/disulfide system plays a role in the formal reduction of the mercury dication in the gas phase. Occurrence of complementary sulfenium and protonated thiol fragments in the spectra of protonated disulfides of the

  为了更好地理解金属-生物硫醇缀合物的断裂过程及其生物学意义，已对重金属的谷胱甘肽共轭物，谷胱甘肽代谢瘤的几种硫醇和二硫键进行了能量分辨质谱研究。γ-谷氨酰基化合物的主要裂解过程（无论是硫醇，二硫键，硫醚还是金属-双-硫醇盐形式）都是γ-谷氨酰基残基的损失，ERMS数据表明该过程几乎不受硫取代的影响。但是，单-S-谷胱甘肽-汞（II）阳离子损失的γ-谷氨酰基残基是一个高能的过程，可能表明羧基与金属的强配位。而且，含有γ-谷氨酰基残基的离子失去中性汞而生成a阳离子的过程比不含有them阳离子的过程要高得多，这表明硫醇/二硫化物系统的氧化还原电位在汞的形式还原中发挥了作用气相中的指示。谷胱甘肽代谢瘤的质子化二硫化物光谱中互补sulf和质子化硫醇片段的出现反映了硫醇/二硫化物氧化还原过程的生物学重要性。碎片的强度比与相应氧化还原对溶液中的还原电位成正比。这一发现可以计算出以前未报告的半胱氨酸甘氨酸
• Electroretinogram B-Wave Amplitude in Panic Disorder
  作者：Paolo Castrogiovanni、Fulvio Pieraccini、Sonia Iapichino、Claudia Pacchierotti、Letizia Bossini、Elisabetta Truglia、Claudio Malpassi、Bruno Natale

  DOI：10.1017/s1092852900008580

  日期：2001.3

  Abnormal light-related behaviors have been described for patients with panic disorder (PD). The present study was undertaken to investigate the retinal light response in PD using electroretinography (ERG). The authors conducted bwave ERG measurements with a bright light (after dark adaptation) in 28 patients with PD and 28 control subjects. There were no significant differences in the mean b-wave amplitude between the two groups, but the retinal response to light in PD patients was generally lower than in healthy subjects. A large interindividual variability was found; also noted was a significant difference in the mean b-wave amplitude between the right and left eyes in the control group. The data indicate subtle variation of retinal photosensitivity in a subgroup of patients with PD. Because dopaminergic retinal activity affects b-ERG amplitude, the authors hypothesize that the dopaminergic system is involved in the response to light in PD patients.

  摘要 已描述过惊恐障碍（PD）患者与光有关的异常行为。本研究利用视网膜电图（ERG）对惊恐障碍患者的视网膜光反应进行了研究。作者对 28 名 PD 患者和 28 名对照组受试者进行了强光下（暗适应后）的 b 波 ERG 测量。两组患者的平均 b 波振幅无明显差异，但帕金森病患者视网膜对光线的反应普遍低于健康人。研究发现，个体间的差异很大；同时还注意到，对照组中左右眼的平均 b 波振幅存在明显差异。这些数据表明，视网膜光敏性在帕金森病患者中存在微妙的变化。由于多巴胺能视网膜活动会影响 b-ERG 波幅，作者推测多巴胺能系统参与了帕金森病患者对光的反应。
• GeneANOVA—gene expression analysis of variance
  作者：G. Didier、P. Brézellec、E. Remy、A. Hénaut

  DOI：10.1093/bioinformatics/18.3.490

  日期：2002.3.1

  Summary: GeneANOVA is an ANOVA-based software devoted to the analysis of gene expression data.

  Availability: GeneANOVA is freely available on request for non-commercial use.

  Contact: [e-mail]

  摘要：GeneANOVA是一款基于ANOVA的软件，专门用于分析基因表达数据。

  可用性：GeneANOVA可根据要求免费提供给非商业用户使用。

  联系方式：[e-mail]

• Carnosine dipeptidase II (CNDP2) protects cells under cysteine insufficiency by hydrolyzing glutathione-related peptides
  作者：Sho Kobayashi、Takujiro Homma、Nobuaki Okumura、Jia Han、Keita Nagaoka、Hideyo Sato、Hiroyuki Konno、Sohsuke Yamada、Toshifumi Takao、Junichi Fujii

  DOI：10.1016/j.freeradbiomed.2021.07.036

  日期：2021.10

  macrophages. The elevation in the CNDP2 protein levels was confirmed by immunoblot analyses and this elevation was accompanied by an increase in hydrolytic activity towards cysteinylglycine, the intermediate degradation product of glutathione after the removal of the γ-glutamyl group, in xCT KO macrophages. Supplementation of the cystine-free media of Hepa1-6 cells with glutathione or cysteinylglycine extended

  胱氨酸转运蛋白 xCT 的敲除 (KO) 在小鼠胚胎成纤维细胞中导致铁死亡，一种铁依赖性坏死细胞死亡，但这不会发生在巨噬细胞中。在这项研究中，我们使用蛋白质组学方法探索了在 xCT 缺陷下支持细胞存活的基因。通过液相色谱-质谱法对用 iTRAQ 标记的巨噬细胞衍生肽进行的分析显示，xCT KO 巨噬细胞中肌肽二肽酶 II (CNDP2) 的水平显着升高。CNDP2 蛋白水平的升高通过免疫印迹分析得到证实，这种升高伴随着对半胱氨酰甘氨酸的水解活性增加，半胱氨酰甘氨酸是 xCT KO 巨噬细胞中去除 γ-谷氨酰基团后谷胱甘肽的中间降解产物。用谷胱甘肽或半胱氨酰甘氨酸补充 Hepa1-6 细胞的无胱氨酸培养基延长了它们的存活时间，而加入 beastatin（一种 CNDP2 抑制剂）则抵消了这些化合物的作用。我们通过 CRISPR/Cas9 系统建立了 CNDP2 KO 小鼠，发现肝脏、肾脏和大脑中的二肽酶活性降低。对乙酰氨基酚过量
• Charge transfer in peptides. Effects of temperature, peptide length and solvent conditions upon intramolecular one-electron reactions involving tryptophan and tyrosine
  作者：Walter A. Prütz、Edward J. Land、Robert W. Sloper

  DOI：10.1039/f19817700281

  日期：——

  oxidised selectively at the indole group with electron accepting radicals (N˙3 or Br˙–2) in aqueous solution, using pulse radiolysis techniques. Subsequent to the primary oxidation an efficient synchronous transformation of indolyl into phenoxyl radicals occurred, both in the linear peptides (n= 0, 1 and 2), [graphic omitted] and in c-TrpH-TyrOH. Rate constants of the reactions [1(n)], obtained by kinetic

  色氨酰-酪氨酰肽，TrpH-（甘氨酸）ñ -TyrOH和环状的C-TrpH-酪氨酸反应，均在吲哚基团选择性氧化用（N电子接受基团˙ 3或Br ˙- 2）在水溶液中，使用脉冲辐解技术。初次氧化后，线性肽段（n = 0、1和2），[c-TrpH-TyrOH]中都发生了吲哚基向苯氧基的有效同步转化。通过动力学吸收光谱法获得的反应[1（n）]的速率常数遵循经验平方反比关系，k 1（n） / k 1（0）= 1 /（1 + n 2/2），k 1（0） = 7.3×10 4 s –1。观察到反应[1（0）]的热活化，其表观活化能为0.22 eV。添加1.5 mol dm –3尿素（氢键结构的改性剂）或60 mmol dm –3 SDS（​​屏蔽疏水性吲哚和酚基的去污剂）不会影响反应[1（0）]。TyrOH的OH基团的去质子化（p K a = 10.1）和吲哚基的质子化（p K a = 4.3）有效地提高了自由基的转化率（k