N-BSMOC-L-丙氨酸 | 197245-15-1

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 丙氨酸类衍生物
• 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-L-丙氨酸
• 中文别名: N-Bsmoc-L-丙氨酸
• 英文名称: Bsmoc-Ala-OH
• 英文别名: N-Bsmoc-L-alanine；(2S)-2-[(1,1-dioxo-1-benzothiophen-2-yl)methoxycarbonylamino]propanoic acid
• CAS: 197245-15-1
• 化学式: C₁₃H₁₃NO₆S
• 分子量: 311.315
• InChiKey: IUXPMHYMBNZBSO-QMMMGPOBSA-N

物化性质

• 熔点：
  105-107°C
• 稳定性/保质期：
  避还原剂

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 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-L-丙氨酸 在 氯化亚砜 作用下， 生成
  参考文献：
  名称：

  Synthesis of N-urethane Protected β-Amino Alcohols Employing N-(protected-α-aminoacyl)benzotriazoles

  摘要：

  通过还原相应的易于获得的 N-酰基苯并三唑，描述了一种简单且无外消旋化的 N-氨基/肽基醇的合成方法。该方法实用、直接、快速、高效，适用于合成氨基/肽醇。所有制得的醇都以高产率和高纯度分离出来。

  DOI：

  10.3184/030823407x272985
• 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-L-丙氨酸
  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

• Multi-arm polymeric conjugates of 7-ethyl-10-hydroxycamptothecin for treatment of breast, colorectal, pancreatic, ovarian and lung cancers
  申请人：Zhao Hong

  公开号：US20070197575A1

  公开（公告）日：2007-08-23

  A four arm-polyethylene glycol-7-ethyl-10-hydroxycamptothecin conjugate, such as, is disclosed. Methods of making the conjugates and methods of treating mammals using the same are also disclosed.

  披露了一种四臂聚乙二醇-7-乙基-10-羟基喜树碱共轭物，以及制备这些共轭物的方法和利用它们治疗哺乳动物的方法。
• [EN] METHOD OF TREATING RAS ASSOCIATED CANCER<br/>[FR] MÉTHODE DE TRAITEMENT DU CANCER ASSOCIÉ AU GÈNE RAS
  申请人：HORAK IVAN

  公开号：WO2010025337A1

  公开（公告）日：2010-03-04

  New methods of treating Ras associated cancer, and especially for treating cancer that is resistant or refractory to other treatment methods, including resistant or refractory to treatment with C225 and/or CPT-11, are provided. The new methods employ PEG-conjugated 7-ethyl-10-hydroxycampothecin, alone, or in combination with other art-known anticancer agents or modalities.

  治疗与Ras相关的癌症的新方法，特别是用于治疗对其他治疗方法具有抗药性或难治性的癌症，包括对C225和/或CPT-11治疗具有抗药性或难治性的癌症。这些新方法利用PEG-共轭的7-乙基-10-羟基喜树碱，单独或与其他已知的抗癌药物或疗法结合使用。
• Dicyclopropylmethyl Peptide Backbone Protectant^†
  作者：Louis A. Carpino、Khaled Nasr、Adel Ali Abdel-Maksoud、Ayman El-Faham、Dumitru Ionescu、Peter Henklein、Holger Wenschuh、Michael Beyermann、Eberhard Krause、Michael Bienert

  DOI：10.1021/ol901310q

  日期：2009.8.20

  The N-dicyclopropylmethyl (Dcpm) residue, introduced into amino acids via reaction of dicyclopropylmethanimine hydrochloride with an amino acid ester followed by sodium cyanoborohydride or triacetoxyborohydride reduction, can be used as an amide bond protectant for peptide synthesis. Examples which demonstrate the amelioration of aggregation effects include syntheses of the alanine decapeptide and the prion peptide (106-126). Avoidance of cyclization to the aminosuccinimide followed substitution of Fmoc-(Dcpm)Gly-OH for Fmoc-Gly-OH in the assembly of sequences containing the sensitive Asp-Gly unit.
• Surcshbabu, Vommina V.; Sudarshan; Chennakrishnareddy, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 4, p. 574 - 579
  作者：Surcshbabu, Vommina V.、Sudarshan、Chennakrishnareddy

  DOI：——

  日期：——
• Synthesis of N-urethane Protected β-Amino Alcohols Employing <i>N</i>-(protected-α-aminoacyl)benzotriazoles
  作者：Vommina V. Sureshbabu、N.S. Sudarshan、L. Muralidhar、N. Narendra

  DOI：10.3184/030823407x272985

  日期：2007.12

  A simple and racemisation-free synthesis of N-urethane protected α-amino/peptidyl alcohols by the reduction of the corresponding easily accessible N-acylbenzotriazoles is described. The method is practical, straightforward, fast and efficient for the synthesis of amino/peptidyl alcohols. All the alcohols made were isolated in high yields and purity.

  通过还原相应的易于获得的 N-酰基苯并三唑，描述了一种简单且无外消旋化的 N-氨基/肽基醇的合成方法。该方法实用、直接、快速、高效，适用于合成氨基/肽醇。所有制得的醇都以高产率和高纯度分离出来。