3-borono-N(α)-tert-butoxycarbonyl-4-methoxy-L-tyrosinate | 606139-97-3

• 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: 3-borono-N(α)-tert-butoxycarbonyl-4-methoxy-L-tyrosinate
• 英文别名: Boc-Tyr(3-B(OH)₂,Me)-OMe；[2-methoxy-5-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]phenyl]boronic acid
• CAS: 606139-97-3
• 化学式: C₁₆H₂₄BNO₇
• 分子量: 353.18
• InChiKey: WKIPZECZWAIROI-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.02
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-borono-N(α)-tert-butoxycarbonyl-4-methoxy-L-tyrosinate 在 盐酸 、 copper diacetate 、 4 Angstroem MS 、 水 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (9S,12S)-12-[N-(tert-butyloxycarbonyl)amino]-2,11-dioxo-4-methoxy-9-methoxycarbonyl-10-azatricyclo[12.2.2.1^3,7]nonadeca-3,5,7(19),14,16,17-hexaene
  参考文献：
  名称：

  Synthesis of l,l-cycloisodityrosines by copper(II) acetate-DMAP-mediated intramolecular O-arylation of phenols with phenylboronic acids

  摘要：

  Two types of cycloisodityrosines, 11 and 13, were synthesized from commercially available chiral tyrosine derivatives through the copper(II) acetate-DMAP-mediated diaryl ether formation of boronotyrosyltyrosines 8 and 10, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01390-x
• 作为产物：
  描述：

  (S )-methyl 2-((tert-butoxycarbonyl)amino)-3-(3-iodo-4-methoxyphenyl)propanoate 在 sodium periodate 、 ammonium acetate 、 potassium acetate 、 palladium dichloride 作用下， 以 水 、 二甲基亚砜 、 丙酮 为溶剂， 生成 3-borono-N(α)-tert-butoxycarbonyl-4-methoxy-L-tyrosinate
  参考文献：
  名称：

  Synthesis of l,l-cycloisodityrosines by copper(II) acetate-DMAP-mediated intramolecular O-arylation of phenols with phenylboronic acids

  摘要：

  Two types of cycloisodityrosines, 11 and 13, were synthesized from commercially available chiral tyrosine derivatives through the copper(II) acetate-DMAP-mediated diaryl ether formation of boronotyrosyltyrosines 8 and 10, respectively. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01390-x

文献信息

• Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine moiety
  作者：Iteng Ng-Choi、Àngel Oliveras、Lidia Feliu、Marta Planas

  DOI：10.3762/bjoc.15.72

  日期：——

  A methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr motif has been devised. This approach comprises two key steps. The first one involves the cyclization of a linear peptidyl resin containing the corresponding halo- and boronoamino acids via a microwave-assisted Suzuki–Miyaura cross coupling. This step is followed by the macrolactamization

  已经设计了用于固相合成包含Phe-Phe，Phe-Tyr或Tyr-Tyr基序的联芳基双环肽的方法。该方法包括两个关键步骤。第一个涉及通过微波辅助的Suzuki-Miyaura交叉偶联环化包含相应的卤代和硼酸氨基酸的线性肽基树脂。该步骤之后是所得到的联芳基单环肽基树脂的大内酰胺化，导致形成了预期的联芳基双环肽。这项研究提供了这种双环化合物的首次固相合成，适合于制备各种合成的或天然的双芳基双环肽。
• Solid-phase synthesis of biaryl cyclic peptides containing a histidine-tyrosine linkage
  作者：Iteng Ng-Choi、Àngel Oliveras、Marta Planas、Lidia Feliu

  DOI：10.1016/j.tet.2019.03.014

  日期：2019.5

  A solid-phase strategy for the synthesis of biaryl cyclic peptides containing a side-chain to side-chain His-Tyr linkage was developed. The key step was the macrocyclization of a linear peptidyl resin incorporating a 5-bromohistidine and a 3-boronotyrosine via the formation of the biaryl bond by means of a microwave-assisted Suzuki-Miyaura reaction. This method allowed direct access to biaryl cyclic

  开发了一种固相策略，用于合成包含侧链至侧链His-Tyr连接的联芳基环肽。关键步骤是通过微波辅助的Suzuki-Miyaura反应通过形成联芳基键合并入5-溴组氨酸和3-硼代酪氨酸的线性肽基树脂的大环化。该方法允许直接获得含有3或5个氨基酸环并在N端或C端带有组氨酸残基的联芳基环肽，特别有利于该氨基酸位于C端的类似物。总站。这项研究还有助于建立一种策略，用于合成衍生自天然联芳基双环肽aciculitins的两个半球的联芳基环肽。
• Boronotyrosine, a Borylated Amino Acid Mimetic with Enhanced Solubility, Tumor Boron Delivery, and Retention for the Re-emerging Boron Neutron Capture Therapy Field
  作者：Arthur Raitano、Tioga Martin、Chunying Zhang、Maria-Christina Malinao、Linnette Capo、Maki Ikeura、Rebecca Carroll、Jason C. Quintana、Samkeliso Dlamini、Leila Kulenovic、Eva Jahanshir、Sohye Kang、Karen Morrison、Michael Torgov、Kendall Morrison

  DOI：10.1021/acs.jmedchem.3c01265

  日期：2023.10.12

  increased cellular retention. Like BPA, BTS uptake is mediated by the l-type amino acid transporter-1 (LAT1) but is less sensitive to natural amino acid competition. BTS can be formulated and bolus dosed at much higher levels than BPA, resulting in 2–3 times greater boron delivery in vivo. Fast blood clearance and greater tumor boron delivery result in superior tumor-to-blood ratios. BTS boron delivery

  硼中子捕获疗法 (BNCT) 是一种重新出现的二元细胞水平癌症干预措施，通过癌症特异性10硼 ( 10 B) 药物和中子的相互作用而发生。我们创造了一种新的10 B 药物 3-硼醇-l-酪氨酸 (BTS)，它改进了主要历史 BNCT 药物 4-硼醇-l-苯丙氨酸 (BPA) 的特性。BTS 的体外吸收量比 BPA 高 4 倍，并且细胞保留能力更强。与 BPA 一样，BTS 摄取由L型氨基酸转运蛋白 1 (LAT1) 介导，但对天然氨基酸竞争不太敏感。BTS 的配制和推注剂量可以比 BPA 高得多，从而使体内硼输送量增加 2-3 倍。快速的血液清除和更多的肿瘤硼输送导致优异的肿瘤与血液比率。BTS 硼输送似乎与 LAT1 表达相关。BTS 是一种很有前途的硼输送药物，有潜力改善现代 BNCT 干预措施。
• Solid-phase synthesis of 5-arylhistidines via a microwave-assisted Suzuki–Miyaura cross-coupling
  作者：Vanessa Cerezo、Muriel Amblard、Jean Martinez、Pascal Verdié、Marta Planas、Lidia Feliu

  DOI：10.1016/j.tet.2008.08.077

  日期：2008.11

  Microwave irradiation efficiently promoted the solid-phase Suzuki-Miyaura reaction of a 5-bromohistidine with various arylboronic acids in the presence of a palladium catalyst. This methodology allowed the synthesis of peptides bearing a histidine residue substituted at position 5 of the imidazole ring with a phenyl, a substituted phenyl, a pyridyl, or a thienyl ring, as well as with the benzene ring of a tyrosine residue. (c) 2008 Elsevier Ltd. All rights reserved.
• [EN] BORYLATED AMINO ACID COMPOSITIONS COMPRISING BTS AND BTS(OME) FOR USE IN BORON NEUTRON CAPTURE THERAPY AND METHODS THEREOF<br/>[FR] COMPOSITIONS D'ACIDES AMINÉS BORYLÉS À BASE DE BTS ET DE BTS(OME) DESTINÉES À ÊTRE UTILISÉES DANS UNE THÉRAPIE CAPTURE DE NEUTRONS DE BORE ET PROCÉDÉS ASSOCIÉS
  申请人：[en]TAE LIFE SCIENCES

  公开号：WO2023009172A1

  公开（公告）日：2023-02-02

  Borylated Amino Acid compositions comprising tyrosine derivatives BTS and BTS(OMe) and novel methods of making BTS and BTS(OMe) are disclosed herein. Consequently, the BTS and/or BTS(OMe) can be scaled up to commercial scale and administered to patients as a Neutron Capture Agent and provide a method of treating cancer, immunological disorders, and other disease by utilizing a Neutron Capture Therapy modality.