N-BSMOC-甘氨酸 | 197245-13-9

• 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: N-BSMOC-甘氨酸
• 中文别名: N-Bsmoc-甘氨酸
• 英文名称: Bsmoc-Gly-OH
• 英文别名: BsmocGlycine；2-[(1,1-Dioxo-1-benzothiophen-2-yl)methoxycarbonylamino]acetic acid
• CAS: 197245-13-9
• 化学式: C₁₂H₁₁NO₆S
• 分子量: 297.288
• InChiKey: DBOLZWJIOHWPHC-UHFFFAOYSA-N

物化性质

• 熔点：
  161-163°C

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  118
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 安全说明：
  S22,S24/25

反应信息

• 作为反应物：
  描述：

  N-BSMOC-甘氨酸 在 吡啶 、 三聚氟氰 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 生成 Bsmoc-Gly-Gly-OEt
  参考文献：
  名称：

  The 1,1-Dioxobenzo[b]thiophene-2-ylmethyloxycarbonyl (Bsmoc) Amino-Protecting Group

  摘要：

  Full details are presented for use of the Bsmoc amino-protecting group for both solid phase and rapid continuous solution syntheses. Application to the latter methodology represents a significant improvement over the corresponding Fmoc-based method for rapid solution synthesis due to the opportunity to use water or saturated sodium-chloride solution rather than an acidic phosphate buffer to remove all byproducts, with consequent cleaner phase separation and higher yields of the growing peptide. Comparison of the Bsmoc and Bspoc functions showed that the former, because of steric hindrance, does not suffer from the competitive or premature deblocking observed with the Bspoc system. Because of its incorporation of a styrene chromophore, resin loading of Bsmoc amino acids could be followed as has previously been shown for the Fmoc analogues. Applications of Bsmoc chemistry to peptide sequences incorporating the base sensitive Asp-Gly unit gave less contamination due to aminosuccinimide formation than comparable syntheses involving standard Fmoc chemistry because a weaker or less concentrated base could be used in the deblocking step. Experimental details are presented for building up peptides in solution via the continuous methodology. Deblockings involved the use of insoluble piperazino silica as well as the polyamine TAEA which simplified aqueous separation of the growing, but nonisolated peptide product, from excess acylating agent and other side products formed in the deblocking process. By the appropriate choice of base, one can act selectively at either site of a molecule which incorporates both beta-elimination and Michael acceptor sites as protective units (Bsmoc vs Fm and Fmoc vs Bsm).

  DOI：

  10.1021/jo982140l
• 作为产物：
  描述：

  benzothiophen-2-yllithium 在 sodium perborate 、 sodium tetrahydroborate 、 三甲基氯硅烷 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 2.0h， 生成 N-BSMOC-甘氨酸
  参考文献：
  名称：

  The 1,1-Dioxobenzo[b]thiophene-2-ylmethyloxycarbonyl (Bsmoc) Amino-Protecting Group

  摘要：

  Full details are presented for use of the Bsmoc amino-protecting group for both solid phase and rapid continuous solution syntheses. Application to the latter methodology represents a significant improvement over the corresponding Fmoc-based method for rapid solution synthesis due to the opportunity to use water or saturated sodium-chloride solution rather than an acidic phosphate buffer to remove all byproducts, with consequent cleaner phase separation and higher yields of the growing peptide. Comparison of the Bsmoc and Bspoc functions showed that the former, because of steric hindrance, does not suffer from the competitive or premature deblocking observed with the Bspoc system. Because of its incorporation of a styrene chromophore, resin loading of Bsmoc amino acids could be followed as has previously been shown for the Fmoc analogues. Applications of Bsmoc chemistry to peptide sequences incorporating the base sensitive Asp-Gly unit gave less contamination due to aminosuccinimide formation than comparable syntheses involving standard Fmoc chemistry because a weaker or less concentrated base could be used in the deblocking step. Experimental details are presented for building up peptides in solution via the continuous methodology. Deblockings involved the use of insoluble piperazino silica as well as the polyamine TAEA which simplified aqueous separation of the growing, but nonisolated peptide product, from excess acylating agent and other side products formed in the deblocking process. By the appropriate choice of base, one can act selectively at either site of a molecule which incorporates both beta-elimination and Michael acceptor sites as protective units (Bsmoc vs Fm and Fmoc vs Bsm).

  DOI：

  10.1021/jo982140l

文献信息

• [EN] CYCLODEXTRIN-BASED POLYMERS FOR THERAPEUTIC DELIVERY<br/>[FR] POLYMÈRES À BASE DE CYCLODEXTRINE POUR UNE ADMINISTRATION THÉRAPEUTIQUE
  申请人：CERULEAN PHARMA INC

  公开号：WO2011063421A1

  公开（公告）日：2011-05-26

  Methods and compositions relating to CDP-taxane conjugates are described herein.

  这里描述了与CDP-紫杉醇共轭物相关的方法和组合物。
• [EN] METHODS OF TREATING A SUBJECT AND RELATED PARTICLES, POLYMERS AND COMPOSITIONS<br/>[FR] MÉTHODES DE TRAITEMENT D'UN SUJET ET PARTICULES, POLYMÈRES ET COMPOSITIONS À CET EFFET
  申请人：FETZER OLIVER S

  公开号：WO2012044832A1

  公开（公告）日：2012-04-05

  Described herein are methods for treating a subject with combinations of polymer-agent particles and cyclodextrin polymer agent conjugates. The methods herein may be used to treat subjects identified with cancer, cardiovascular disorders, autoimmune disorders, or inflammatory disorders. Also described herein are compositions, dosage forms, and kits comprising polymer-agent particles and cyclodextrin polymer agent conjugates.

  本文描述了一种利用聚合物-药剂颗粒和环糊精聚合物药剂共轭物组合治疗受试者的方法。本文中的方法可用于治疗被诊断患有癌症、心血管疾病、自身免疫性疾病或炎症性疾病的受试者。本文还描述了包含聚合物-药剂颗粒和环糊精聚合物药剂共轭物的组合物、剂型和配套工具。
• CYCLODEXTRIN-BASED POLYMERS FOR THERAPEUTIC DELIVERY
  申请人：CERULEAN PHARMA INC.

  公开号：US20130196946A1

  公开（公告）日：2013-08-01

  Methods and compositions relating to CDP-taxane conjugates are described herein.

  本文描述了与CDP-紫杉醇共轭物相关的方法和组合物。
• Methods of preparing amino acid taxane derivatives and polymer conjugates containing the same
  申请人：Enzon, Inc.

  公开号：US06649778B1

  公开（公告）日：2003-11-18

  Methods of preparing amino acid-substituted taxanes such as: using selected blocked amino acids are disclosed. After coupling of the blocked amino acid to the taxane, deprotection is carried out with about an equimolar amount of a secondary amine thus substantially avoiding base-catalyzed hydrolysis of amino acid from the taxane. The preferred amino acid-taxanes are useful as intermediates in the production of polymer conjugated therapeutic compositions or as part of pharmaceutically acceptable formulations.

  公开了制备氨基酸取代紫杉醇的方法，例如：使用选择的保护氨基酸。在将保护氨基酸与紫杉醇偶联后，用约等摩尔量的二级胺进行脱保护，从而基本避免了在紫杉醇中发生碱催化的氨基酸水解。首选的氨基酸-紫杉醇可用作生产聚合物结合的治疗组合物的中间体或作为药用可接受的配方的一部分。
• METHODS OF TREATING A SUBJECT AND RELATED PARTICLES, POLYMERS AND COMPOSITIONS
  申请人：Fetzer Oliver S.

  公开号：US20120213854A1

  公开（公告）日：2012-08-23

  Described herein are methods for treating a subject with combinations of polymer-agent particles and cyclodextrin polymer agent conjugates. The methods herein may be used to treat subjects identified with cancer, cardiovascular disorders, autoimmune disorders, or inflammatory disorders. Also described herein are compositions, dosage forms, and kits comprising polymer-agent particles and cyclodextrin polymer agent conjugates.

  本文介绍了使用聚合物-药剂颗粒和环糊精聚合物药剂共轭物的组合治疗方法来治疗患有癌症、心血管疾病、自身免疫性疾病或炎症性疾病的受试者。本文还描述了包含聚合物-药剂颗粒和环糊精聚合物药剂共轭物的组合物、剂型和套装。