S-palmitoyl-L-cysteine | 114507-35-6

• 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
• 英文名称: S-palmitoyl-L-cysteine
• 英文别名: Boc-Cys(Palm)-OH；(2R)-2-amino-3-hexadecanoylsulfanylpropanoic acid
• CAS: 114507-35-6
• 化学式: C₁₉H₃₇NO₃S
• 分子量: 359.574
• InChiKey: FRAMWPHPFIXRCP-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  棕榈酸酐 、 Boc-S-叔-丁基巯基-L-半胱氨酸 在 N,N-二异丙基乙胺 、 1,4-dithio-D,L-threitol 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 以87 %的产率得到S-palmitoyl-L-cysteine
  参考文献：
  名称：

  通过基于 Boc-SPPS 的肽 C 端水杨醛酯的一般策略实现具有碱基不稳定翻译后修饰的蛋白质的化学合成

  摘要：

  开发了一种基于 Boc-SPPS 的方法来合成与所有规范氨基酸相容的肽 C 末端水杨醛酯。该方法可以促进带有碱不稳定翻译后修饰的蛋白质的合成，例如，O-乙酰化和S-棕榈酰化。

  DOI：

  10.1002/anie.202214053

文献信息

• SYNTHETIC SUBSTRATES FOR ENZYMES THAT CATALYZE REACTIONS OF MODIFIED CYSTEINES AND RELATED METHODS
  申请人：The University of Chicago

  公开号：US20180147250A1

  公开（公告）日：2018-05-31

  Synthetic probes for detecting the activity of enzymes that catalyze reactions of post-translationally modified cysteine residues are described. The probes include “turn-on” probes that include a carbamate linkage that is cleaved via an intramolecular reaction with a free thiol produced by an enzyme catalyzed activity. The probes also include ratiometric, Michael addition-based probes that respond to enzymatic activity by a change in structure that results in a change in fluorescence properties. Methods of using the probes to detect enzymatic activity and disease are described. For example, the probes can be used to detect enzymatic activity in a variety of samples, including live cells and heterogeneous tissues. In addition, prodrugs that can be activated by enzymes that catalyze reactions of post-translationally modified cysteine residues and methods of using the prodrugs to treat disease are described.

  描述了用于检测催化后翻译修饰半胱氨酸残基反应活性的酶的合成探针。这些探针包括“开启”探针，其中包括通过酶催化活性产生的游离巯基进行分子内反应从而裂解的碳酸酯连接。这些探针还包括比例计量、基于迈克尔加成的探针，通过结构的变化响应酶活性，导致荧光特性的变化。描述了使用这些探针检测酶活性和疾病的方法。例如，这些探针可用于检测各种样本中的酶活性，包括活细胞和异质组织。此外，还描述了可以由催化催化后翻译修饰半胱氨酸残基反应的酶激活的前药和使用这些前药治疗疾病的方法。
• Peptide Tyrosinase Activators
  申请人：Escape Therapeutics, Inc.

  公开号：US20150152139A1

  公开（公告）日：2015-06-04

  Peptides that increase melanin synthesis are provided. These peptides include pentapeptides YSSWY, YRSRK, and their variants. The peptides may activate the enzymatic activity of tyrosinase to increase melanin synthesis. The pharmaceutical, cosmetic, and other compositions including the peptides are also provided. The methods of increasing melanin production in epidermis of a subject are provided where the methods include administering compositions comprising an amount of one or more peptides effective to increase the melanin production. The methods also include treating vitiligo or other hypopigmentation disorders with compositions including one or more peptides.

  提供了增加黑色素合成的肽类。这些肽包括五肽YSSWY、YRSRK及其变体。这些肽可能激活酪氨酸酶的酶活性，以增加黑色素的合成。还提供了包括这些肽的制药、化妆品和其他组合物。提供了一种增加受试者表皮黑色素产生的方法，其中方法包括给予含有一种或多种肽的组合物的有效量以增加黑色素的产生。这些方法还包括使用包括一种或多种肽的组合物治疗白癜风或其他低色素症。
• Imaging of protease activity in live cells using activity based probes
  申请人：Bogyo S. Matthew

  公开号：US20070036725A1

  公开（公告）日：2007-02-15

  Methods and materials for the imaging of cells containing active proteases such as cathepsin are disclosed. The present materials include activity based probes that bind to an enzyme and are subsequently cleaved. Cleavage results in a fluorescent signal due to removal of a quenching group which, when present on the probe causes altered or no fluorescence. The probes employ an acyloxymethyl ketone reactive group, one or more amino acids for determining specificity, a fluorophore and a quencher. The probes are cell permeable and may use, for example, a QSY7 (diarylyrhodamine) quencher and a BODIPY (bora-diaza-indecene) dye.

  揭示了用于成像含有活性蛋白酶（如半胱氨酸蛋白酶）的细胞的方法和材料。目前的材料包括结合到酶并随后被切割的活性基团探针。切割导致荧光信号的产生，因为去除了一个熄灭基团，当存在于探针上时，会导致改变或无荧光。这些探针使用酰氧甲基酮反应基团，一个或多个氨基酸用于确定特异性，一个荧光团和一个熄灭剂。这些探针具有细胞穿透性，例如，可以使用QSY7（二芳基罗丹明）熄灭剂和BODIPY（硼二氮杂环庚烯）染料。
• Automated identification of peptides
  申请人：——

  公开号：US20020102610A1

  公开（公告）日：2002-08-01

  A fully automated, user-independent method is described for computer-mediated interpretation of data derived by mass spectrometry of an experimental peptide to identify and characterize a corresponding peptide sequence in a peptide database. The method identifies the corresponding sequence if it is present in the database, without the need for a skilled observer to choose from amongst a list of possible matches. By using an automated back-read process, the present method can uniquely identify a corresponding peptide sequence in a database based on a single matching peptide sequence. The method also permits mapping of mass spectral data to sequences in peptide or nucleotide databases for unambiguous identification of exons; determining a correct reading frame; identifying artefacts and errors in sequences; identifying mutations and polymorphisms; identifying post-translational modifications; and identifying exon-intron boundaries.

  本文描述了一种完全自动化、不依赖用户的方法，用于通过质谱技术获得的实验性肽段数据的计算机介导解释，以识别和表征相应的肽段序列在肽段数据库中的对应关系。该方法可以在不需要熟练的观察者从可能匹配的列表中选择的情况下，识别出数据库中存在的相应序列。通过使用自动化的反向读取过程，本方法可以基于单个匹配的肽段序列，在数据库中唯一地识别相应的肽段序列。该方法还允许将质谱数据映射到肽或核苷酸数据库中的序列，以明确识别外显子；确定正确的阅读框架；识别序列中的工件和错误；识别突变和多态性；识别后翻译修饰；以及识别外显子-内含子边界。
• Oligopeptide Tyrosinase Inhibitors and Uses Thereof
  申请人：Hantash Basil M.

  公开号：US20090099091A1

  公开（公告）日：2009-04-16

  Disclosed are peptides that inhibit the enzymatic activity of tyrosinase, as well as formulations and methods for their use in the reduction of skin pigmentation, and methods of administering the inhibitory peptides in a topical formulation. Peptide sequences disclosed include KFEKKFEK and YRSRKYSSWY.

  本发明涉及一种抑制酪氨酸酶酶活性的肽，以及用于减少皮肤色素沉着的配方和方法，以及在局部配方中给予抑制肽的方法。揭示的肽序列包括KFEKKFEK和YRSRKYSSWY。