L-isoleucine, phenylmethyl ester, hydrochloride

• 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: L-isoleucine, phenylmethyl ester, hydrochloride
• 英文别名: benzyl (2S)-2-amino-3-methylpentanoate;hydrochloride
• 化学式: C₁₃H₁₉NO₂*ClH
• 分子量: 257.76
• InChiKey: KGVGWRRIIMXOQH-RLVDVTLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  L-isoleucine, phenylmethyl ester, hydrochloride 在 N-甲基吗啉 、 N-羟基-7-氮杂苯并三氮唑 、 palladium 10% on activated carbon 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 乙二胺 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 40.0 ℃ 、344.75 kPa 条件下， 反应 34.5h， 生成
  参考文献：
  名称：

  Site-Selective C(sp³)–H Functionalization of Di-, Tri-, and Tetrapeptides at the N-Terminus

  摘要：

  Although the syntheses of novel and diverse peptides rely mainly on traditional coupling using unnatural amino acids, postsynthetic modification of peptides could provide a complementary method for the preparation of nonproteinogenic peptides. Site selectivity of postsynthetic modification of peptides is usually achieved by targeting reactive moieties, such as the thiol group of cysteine or the C-2 position of tryptophan. Herein, we report the development of site-selective functionalizations of inert C(sp(3))-H bonds of N-terminal amino acids in di-, tri-, and tetrapeptides without installing a directing group. The native amino acid moiety within the peptide is used as a ligand to accelerate the C-H activation reaction. In the long run, this newly uncovered reactivity could provide guidance for developing site-selective C(sp(3))-H activation toward postsynthetic modification of a broader range of peptides.

  DOI：

  10.1021/ja510233h

文献信息

• Lewis acid-catalyzed cleavage of carbamate and carbonate resins
  作者：Wen-Ren Li、Yu-Sheng Lin、Ying-Chih Yo

  DOI：10.1016/s0040-4039(00)01131-x

  日期：2000.8

  developed. Polymer-supported carbamates react cleanly with zinc bromide and the appropriate acyl halide in the presence of triethylamine to provide their corresponding amides in high yields and purities. Cleavage of resin-bound carbonates was carried out using the similar reagent systems in the absence of triethylamine to give acetates or benzoates.

  已经开发了在Merrifield树脂结合的苄氧羰基当量上制备酰胺和酯的方法。聚合物负载的氨基甲酸酯在三乙胺的存在下与溴化锌和适当的酰卤发生清洁反应，以高收率和纯度提供其相应的酰胺。在不存在三乙胺的情况下，使用类似的试剂系统进行树脂结合的碳酸酯的裂解，从而得到乙酸酯或苯甲酸酯。
• NATARAJAN, SESHA I.;RYONO, DENIS E.;PETRILLO, EDWARD W. (JR)
  作者：NATARAJAN, SESHA I.、RYONO, DENIS E.、PETRILLO, EDWARD W. (JR)

  DOI：——

  日期：——
• [EN] INHIBITORS OF ENDOTHELIN CONVERTING ENZYME<br/>[FR] INHIBITEURS DE L'ENZYME CONVERTISSANT L'ENDOTHELINE
  申请人：WARNER-LAMBERT COMPANY

  公开号：WO1994022906A1

  公开（公告）日：1994-10-13

  (EN) Novel inhibitors of endothelin converting enzyme are described, as well as methods for the preparation and pharmaceutical compositions of the same, which are useful in treating elevated levels of endothelin, acute and chronic renal failure, hypertension, myocardial infarction, metabolic, endocrinological, neurological disorders, congestive heart failure, endotoxic and hemorrhagic shock, subarachnoid hemorrhage, arrhythmias, asthma, preeclampsia, atherosclerotic disorders including Raynaud's disease, restenosis, angina, cancer, pulmonary hypertension, ischemic disease, gastric mucosal damage, ischemic bowel disease, and diabetes.(FR) On décrit de nouveaux inhibiteurs de l'enzyme convertissant l'endothéline ainsi que des procédés de préparation de compositions phamaceutiques de ceux-ci, qui sont praticulièrement utiles pour traiter des niveaux élevés d'endothéline, les défaillances rénales aiguës et chroniques, l'hypertension, les infarctus du myocarde, les désordres métaboliques, endocriniens et neurologiques, l'insuffisance cardiaque, les chocs endotoxiques ou hémorragiques, les hémorragies sous-arachnoïdiennes, l'arythmie, l'asthme, la prééclampsie, les artérioscléroses diverses et en particulier la maladie de Raynaud, les resténoses, l'angine, le cancer, l'hypertension pulmonaire, les maladies ischémiques, les atteintes de la muqueuse gastrique, les maladies ischémiques de l'intestin et le diabète.