N-ε-D-Cbz-lysine | 34404-32-5

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 赖氨酸类衍生物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-ε-D-Cbz-lysine
• 英文别名: H-D-Lys(Z)-OH；(2R)-2-amino-6-(phenylmethoxycarbonylamino)hexanoic acid
• CAS: 34404-32-5
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: CKGCFBNYQJDIGS-GFCCVEGCSA-N

物化性质

• 熔点：
  229℃
• 沸点：
  499.6±45.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)
• 稳定性/保质期：

  避免氧化物

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• WGK Germany：
  3
• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  密封，在-20°C下保存

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: H-D-Lys(Z)-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: H-D-Lys(Z)-OH
CAS number: 34404-32-5

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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, refrigerated.
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: C14H20N2O4
Molecular weight: 280.3

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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

制备方法与用途

H-D-Lys(Z)-OH是一种赖氨酸衍生物[1]。

反应信息

• 作为反应物：
  描述：

  N-ε-D-Cbz-lysine 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 2.67h， 生成 N-Boc-N'-Fmoc-D-赖氨酸 N-叔丁氧羰基-N'-芴甲氧羰基-D-赖氨酸
  参考文献：
  名称：

  Solid-Phase Total Synthesis of Oscillamide Y and Analogues

  摘要：

  We report an efficient solid phase synthesis of oscillamide Y and three analogues. The cyclic peptide was prepared using a combination of Fmoc and allyl chemistries and an acid labile Wang type linker. The urea functionality was smoothly incorporated using N-alpha-(4-nitrophenyloxycarbonyl)-N-epsilon-(9-fluorenylmethoxycarbonyl)-D-lysine allyl ester. Coupling to the N-methyl amino acid was readily achieved using HATU, monitoring the reaction using bromophenol blue. Allyl deprotection was accomplished using Pd(PPh3)(4) and dimedone, and cyclization was smoothly accomplished using PyBroP. All reactions were monitored using mass spectrometry methodology. The cyclized materials were cleaved by acidolysis and purified by RP HPLC. In all cases the material isolated was the major product and gave the expected molecular ion information. HPLC comparison with an authentic sample of oscillamide Y showed that the isomer containing L-N-methylalanine and L-homotyrosine was the natural product. H-1 NMR and H-1-H-1 COSY NMR experiments further confirmed this identification. The four compounds were tested as competitive and slow-tight binding inhibitors of chymotrypsin but showed, contrary to literature expectations, no inhibitory activity.

  DOI：

  10.1021/jo970671o
• 作为产物：
  描述：

  For-D-Lys(-Z)-OH 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 N-ε-D-Cbz-lysine
  参考文献：
  名称：

  Resolution of α-Formyl-ε-acyl-DL-lysines by Acylase

  摘要：

  Taka-acylase 对 ε-acyl-l-lysine 的 α-formyl 衍生物的水解速度快于相应的 α-acetyl 衍生物。用粗制的 Takaacylase 进行制备解析，可以从相应的 α-甲酰基-ε-乙酰基-Dl-赖氨酸中得到 ε-甲酰基或 ε-苄氧羰基-l-赖氨酸。对甲苯磺酸在温和条件下作用于 α-甲酰基-ε-苄氧羰基-Dl-赖氨酸，可得到纯的ε-苄氧羰基-Dl-赖氨酸。

  DOI：

  10.1246/bcsj.51.1899

文献信息

• [EN] CONJUGATES COMPRISING PEPTIDE GROUPS AND METHODS RELATED THERETO<br/>[FR] CONJUGUÉS COMPRENANT DES GROUPES PEPTIDIQUES ET PROCÉDÉS ASSOCIÉS À CEUX-CI
  申请人：LEGOCHEM BIOSCIENCES INC

  公开号：WO2017089894A1

  公开（公告）日：2017-06-01

  In some aspects, the invention relates to an antibody-drug conjugate, comprising an antibody; a linker; and at least two active agents. In preferred embodiments, the linker comprises a peptide sequence of a plurality of amino acids, and at least two of the active agents are covalently coupled to side chains of the amino acids. The antibody-drug conjugate may comprise a self-immolative group, preferably two-self-immolative groups. The linker may comprise an O-substituted oxime, e.g., wherein the oxygen atom of the oxime is substituted with a group that covalently links the oxime to the active agent; and the carbon atom of the oxime is substituted with a group that covalently links the oxime to the antibody.

  在某些方面，本发明涉及一种抗体药物偶联物，包括：抗体；连接体；以及至少两个活性剂。在优选的实施例中，连接体包括由多个氨基酸组成的肽序列，其中至少两个活性剂通过共价键与氨基酸的侧链连接。抗体药物偶联物可以包括自焚基团，优选地是两个自焚基团。连接体可以包括O-取代的肟，例如，其中肟的氧原子被取代以与活性剂形成共价键连接；肟的碳原子被取代以与抗体形成共价键连接。
• Synthesis and pharmacological characterization in vitro of cyclic enkephalin analogs: effect of conformational constraints on opiate receptor selectivity
  作者：John DiMaio、Thi M. D. Nguyen、Carole Lemieux、Peter W. Schiller

  DOI：10.1021/jm00354a008

  日期：1982.12

  [D-Leu5] and [des-Leu5] analogues of 4 (5 and 6) showed, in general, high potency in the guinea pig ileum (GPI) assay and low potency in the mouse vas deferens (MVD) assay. IC50 (MVD)/IC50 (GPI) ratios ranging from 3.1 to 29.4 were obtained, indicating the preference of the cyclic analogues for mu receptors over delta receptors. With two exceptions, preferential affinity for mu receptors is reflected in the

  使用固相和溶液方法的组合，我们通过取代脑啡肽序列2位上的D-α，ω-二氨基酸和将ω-氨基环化成环，合成了一系列环状[Leu5]脑啡肽类似物。亮氨酸的C末端羧基。在位置2和[D-Leu5]上包含D-alpha，β-二氨基丙酸（1），D-alpha，γ-二氨基丁酸（2），D-鸟氨酸（3）或D-赖氨酸（4）的环状类似物]和[des-Leu5] 4的类似物（5和6）通常在豚鼠回肠（GPI）分析中显示出高效，而在小鼠输精管（MVD）分析中显示出低效。获得的IC50（MVD）/ IC50（GPI）比率范围为3.1至29.4，表明mu受体比delta受体更喜欢环状类似物。除了两个例外，对mu受体的优先亲和力反映在分别使用[3H]纳洛酮和[3H] [D-Ala2，D-Leu5]脑啡肽作为mu和delta受体选择性放射性配体的平行结合测定中确定的Ki比中。环状类似物1-4与相应的开环类似物[D-Ala2，L
• Use of 2-aminothiazoline derivatives as inhibitors of inducible no-synthase
  申请人：——

  公开号：US20020022631A1

  公开（公告）日：2002-02-21

  The present invention relates to the use of 2-aminothiazoline derivatives of formula: 1 in which either R 1 is a hydrogen atom or an alkyl radical and R 2 is an alkyl, -alk-NH 2 , —CH 2 —R 3 , —CH 2 —S—R 4 or phenyl radical substituted with a nitro or —NH—C(═NH)CH 3 radical, or R 1 is an alkyl radical and R 2 is a hydrogen atom, R 3 is a (3-6C) cycloalkyl, pyridyl, pyridyl N-oxide, thienyl, thiazolyl, imidazolyl, pyrazinyl, triazolyl or phenyl radical or a phenyl radical substituted with a nitro, hydroxy or carboxyl radical, R 4 represents a pyridyl or pyridyl N-oxide radical, alk represents an alkylene radical, or pharmaceutically acceptable salts thereof, as inhibitors of inducible NO-synthase.

  本发明涉及通式1的2-氨基噻唑啉衍生物的用途： 其中，R1为氢原子或烷基基团，R2为烷基、-烷-NH2、—CH2—R3、— —S—R4或被硝基或—NH—C(═NH)CH3基团取代的苯基基团；或者，R1为烷基基团，R2为氢原子，R3为(3-6C)环烷基、吡啶基、吡啶基N-氧化物、噻吩基、噻唑基、咪唑基、吡嗪基、三唑基或苯基基团，或被硝基、羟基或羧基基团取代的苯基基团，R4代表吡啶基或吡啶基N-氧化物基团，烷代表亚烷基基团，或其药学上可接受的盐，作为诱导型NO合酶抑制剂。
• Structure-based design of six novel classes of nonpeptide antagonists of the bradykinin B2 receptor
  作者：Dean R Artis、Christine Brotherton-Pleiss、Joseph H.B Pease、Clara J Lin、Steve W Ferla、Sherry R Newman、Sunil Bhakta、Helene Ostrelich、Kurt Jarnagin

  DOI：10.1016/s0960-894x(00)00482-0

  日期：2000.11

  Six classes of nonpeptide bradykinin antagonists were designed using a template derived from structural studies of peptide antagonists. Several compounds from each class were synthesized and assayed for binding to the human bradykinin B2 receptor. Each family showed compounds active at the level of the smallest template peptide; three classes contained compounds with Kd < 8 microM. These results provide

  使用衍生自肽拮抗剂结构研究的模板设计了六类非肽缓激肽拮抗剂。合成了每种类别的几种化合物，并测定了与人缓激肽B2受体的结合。每个家族均显示出在最小模板肽水平上具有活性的化合物。三类含有Kd <8 microM的化合物。这些结果为基于药物化学的优化程序提供了多种线索。
• Design of fluorogenic probes and fluorescent-tagged inhibitors for<i>γ</i>-glutamyl cyclotransferase
  作者：Taku Yoshiya、Hiromi Ii、Shugo Tsuda、Masayoshi Mochizuki、Susumu Kageyama、Tatsuhiro Yoshiki

  DOI：10.1002/psc.2984

  日期：2017.7

  A tumor‐related protein, human chromosome 7 ORF 24 (C7orf24), is involved in regulation of the glutathione homeostasis cycle as a γ‐glutamyl cyclotransferase (GGCT). The singular substrate preference of this enzyme had long hampered its chemical probe development. That is, substrate of GGCT is definitely ‘γ‐Glu‐Xaa’, where Xaa is an L‐α‐amino acid. Based on the structure of substrates and GGCT fluorogenic

  肿瘤相关蛋白人类染色体7 ORF 24（C7orf24）作为γ-谷氨酰环转移酶（GGCT）参与谷胱甘肽稳态循环的调控。这种酶对底物的偏爱早就阻碍了其化学探针的发展。也就是说，GGCT的底物肯定是“ γ -Glu-Xaa”，其中Xaa是L - α-氨基酸。根据底物和GGCT荧光探针LISA-4 / 101的结构，我们成功开发了一种荧光标记的抑制剂gKFA。这些化学工具将在将来协助癌症相关的研究。版权所有©2017欧洲多肽协会和John Wiley＆Sons，Ltd.