N-(9-fluorenylmethoxycarbonyl)-proline allyl ester | 802918-70-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(9-fluorenylmethoxycarbonyl)-proline allyl ester
• 英文别名: Fmoc-L-Pro-OAll；1-O-(9H-fluoren-9-ylmethyl) 2-O-prop-2-enyl (2S)-pyrrolidine-1,2-dicarboxylate
• CAS: 802918-70-3
• 化学式: C₂₃H₂₃NO₄
• 分子量: 377.44
• InChiKey: PTNWDFUJGMHLPD-NRFANRHFSA-N

物化性质

• 沸点：
  527.6±45.0 °C(Predicted)
• 密度：
  1.227±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(9-fluorenylmethoxycarbonyl)-proline allyl ester 在 [2-(双环己基膦基)乙基]三甲基三甲基氯化铵 、 苯硅烷 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以80%的产率得到Fmoc-L-脯氨酸
  参考文献：
  名称：

  Synthesis of l-Octaarginine through Microencapsulated Palladium-Catalyzed Allyl Ester Deprotection

  摘要：

  Octaarginine has been described as a molecular transporter. We report a useful synthesis of orthogonally protected L-octaarginine by using a method based on a microencapsulated palladium catalyst. Known palladium-based methods for allyl ester deprotection have been modified to facilitate purification of the unprotected intermediates. This improvement in the purification step has also been tested with a variety of allyl alpha-amino esters and allyl alpha,beta-unsaturated esters.

  DOI：

  10.1055/s-0034-1378379
• 作为产物：
  描述：

  Fmoc-L-脯氨酸 、 3-溴丙烯 在 potassium hydrogencarbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 以82%的产率得到N-(9-fluorenylmethoxycarbonyl)-proline allyl ester
  参考文献：
  名称：

  通过Ser / Thr连接进行翻译后修饰的HMGA1a蛋白的化学合成

  摘要：

  据报道，通过Ser / Thr连接进行了核蛋白HMGA1a的首次化学合成。值得注意的是，Hmb（2 - h ydroxy -4- m ethoxy b enzyl）对固相肽合成过程中的困难偶联和蛋白质合成中的不良连接均显示出关键性的改善。这些导致制剂HMGA1a的努力类似物具有良好限定的磷酸化和甲基化模式（总共9个合成的蛋白），因此克服了非均相和组合子固有的问题蛋白p ost-吨ranslational米odifications（翻译后修饰），和促进的研究此类PTM的监管作用。

  DOI：

  10.1021/acs.orglett.6b03056

文献信息

• Oxime-Based Carbonates as Useful Reagents for Both N-Protection and Peptide Coupling
  作者：Yahya Jad、Sherine Khattab、Ayman El-Faham、Fernando Albericio

  DOI：10.3390/molecules171214361

  日期：——

  We have demonstrated that oxime-based mixed carbonates are very effective reagents for both N-protection and peptide coupling.

  我们已经证明，基于肟的混合碳酸盐作为N-保护和肽偶联的试剂非常有效。
• Synthetic Approach Toward the Partial Sequences of Betaglycan in the Linkage Region on Solid Support and in Solution Phase
  作者：Jun‐ichi Tamura、Akihiro Yamaguchi、Junko Tanaka、Yuko Nishimura

  DOI：10.1080/07328300701296810

  日期：2007.4.30

  We have synthesized, for the first time, the partial sequence of the betaglycan composed of the tetraosyl hexapeptide, which was directly usable as a probe for enzymatic glycosyl transfer. Stepwise elongation afforded the corresponding tetraosyl trichloroacetimidate. The common glycosyl dipeptide:[beta-D-GlcA-(1 -> 3)-beta-D-Gal-(1 -> 3)-beta-D-Gal-(1 -> 4)-beta-D- Xyl-(1 -> O)-Ser-Gly] was synthesized by glycosylation of the corresponding tetraosyl trichloroacetimidate and Ser-Gly moiety. The glycosyl dipeptide was coupled with other core peptide parts in solution phase and on a solid support. These glycosyl hexapeptides were then transformed into the desired target compounds.
• [EN] COMPOUNDS & METHODS FOR THE ENHANCED DEGRADATION OF TARGETED PROTEINS & OTHER POLYPEPTIDES BY AN E3 UBIQUITIN LIGASE<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR LA DÉGRADATION AMÉLIORÉE DE PROTÉINES CIBLES ET D'AUTRES POLYPEPTIDES PAR UNE E3 UBIQUITINE LIGASE
  申请人：UNIV YALE

  公开号：WO2013106643A2

  公开（公告）日：2013-07-18

  The present invention relates to bifunctional compounds, which find utility as modulators of targeted ubiquitination, especially inhibitors of a variety of polypeptides and other proteins which are degraded and/or otherwise inhibited by bifunctional compounds according to the present invention. In particular, the present invention is directed to compounds, which contain on one end a VHL ligand which binds to the ubiquitin ligase and on the other end a moiety which binds a target protein such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of that protein. The present invention exhibits a broad range of pharmacological activities associated with compounds according to the present invention, consistent with the degradation/inhibition of targeted polypeptides.
• [EN] COMPOUNDS AND METHODS FOR THE INHIBITION OF VCB E3 UBIQUITIN LIGASE<br/>[FR] COMPOSÉS ET PROCÉDÉS POUR L'INHIBITION DE L'UBIQUITINE LIGASE VCB E3
  申请人：UNIV YALE

  公开号：WO2013106646A2

  公开（公告）日：2013-07-18

  The present invention relates to novel compounds which find utility as modulators, especially inhibitors of VCB E3 Ubiquitin Ligase and as bioactive agents for use as therapeutics for the stimulation of erythropoiesis in a patient or subject including inducement of EPO production in the patient or subject, for the treatment of chronic anemia and ischemia (limits brain injury during episodes of localized anemia, ischemia and/or stroke and damage to cardiovascular tissue during cardiovascular ischemia), as well as enhancing wound healing processes. Pharmaceutical compositions comprising effective amounts of compounds according to the present invention alone or in combination with an additional erythropoieses stimulating agent such as EPO under the tradename procrit or epogen or darbapoietin alfa under the tradename aranesp. Methods of stimulating erythropoiesis in a subject or patient, including increasing the number of red blood cells and/or hematocrit of the patient, treating anemia, including chronic anemia and anemia associated with chronic kidney disease, dialysis, and cancer chemotherapy, ischemia, stroke and damage to cardiovascular tissue during cardiovascular ischemia as well as enhancing wound healing processes and preventing/reducing scarring secondary to healing represent additional aspects of the present invention. Local enhancement of angiogenesis through induction of VEGF including wound healing and reduction of stent occlusion remain additional aspects of the present invention.
• [EN] METHOD FOR PRODUCING PEPTIDE COMPOUND CONTAINING N-SUBSTITUTED-AMINO ACID RESIDUE<br/>[FR] PROCÉDÉ DE PRODUCTION D'UN COMPOSÉ PEPTIDIQUE CONTENANT UN RÉSIDU D'ACIDE AMINÉ N-SUBSTITUÉ<br/>[JA] Ｎ－置換－アミノ酸残基を含むペプチド化合物の製造方法
  申请人：[en]CHUGAI SEIYAKU KABUSHIKI KAISHA;[ja]中外製薬株式会社

  公开号：WO2022138891A1

  公开（公告）日：2022-06-30

  本発明は、効率的に高純度のペプチド化合物を高収率で製造する方法を提供することを課題とする。固相法における最初の伸長反応に先立って、ペプチドを固相合成用樹脂に担持させることにより、斯かる課題を解決できることを見出した。