N^α-Carboxy-ornithin, α-Carbamoyl-ornithin | 90027-03-5

• 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: N^α-Carboxy-ornithin, α-Carbamoyl-ornithin
• 英文别名: DL-Isocitrullin；5-Amino-2-(carbamoylamino)pentanoic acid
• CAS: 90027-03-5
• 化学式: C₆H₁₃N₃O₃
• 分子量: 175.188
• InChiKey: IXXSOHKFCZVUSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  L-3-Ureido-piperidon 在 sodium hydroxide 作用下， 生成 N^α-Carboxy-ornithin, α-Carbamoyl-ornithin
  参考文献：
  名称：

  The Reaction of Cyanogen Bromide with Mono- and Diamino Acids

  摘要：

  DOI：

  10.1021/ja01066a029

文献信息

• [EN] CALICHEAMICIN DERIVATIVES AND ANTIBODY DRUG CONJUGATES THEREOF<br/>[FR] DÉRIVÉS DE CALICHÉAMICINE ET CONJUGUÉS ANTICORPS-MÉDICAMENTS DE CEUX-CI
  申请人：PFIZER

  公开号：WO2018138591A1

  公开（公告）日：2018-08-02

  The present invention is directed to novel calicheamicin derivatives useful as payloads in antibody-drug-conjugates (ADC's), and to payload-linker compounds and ADC compounds comprising the same; to pharmaceutical compositions comprising the same and to methods for using the same to treat pathological conditions such as cancer.

  本发明涉及新型calicheamicin衍生物，用作抗体-药物偶联物（ADC）的有效载荷，以及包含相同有效载荷-连接剂化合物和ADC化合物；涉及包含它们的药物组合物以及使用它们治疗诸如癌症等病理状态的方法。
• [EN] GNRH ANTAGONISTS<br/>[FR] ANTAGONISTES DE LA GONADOLIBERINE
  申请人：THE SALK INSTITUTE FOR BIOLOGICAL STUDIES

  公开号：WO1995025741A1

  公开（公告）日：1995-09-28

  (EN) Analogs of the decapeptide GnRH which include two significantly modified amino acids at positions 5 and 6 inhibit the secretion of gonadotropins by the pituitary gland and inhibit the release of steroids by the gonads. Administration of an effective amount of such GnRH antagonists prevents ovulation of female mammalian eggs and/or the release of steroids by the gonads and may be used to treat steroid-dependent tumors. Particularly effective peptides which are soluble in water at physiologic pH and which have a low tendency to gel when administered $i(in vivo) have the following formula: Ac-$g(b)-D-2NAL-(4C1)D-Phe-D-3PAL-Ser-Aph(Q1)(3-amino-1,2,4-triazole)-D-Aph(Q2)(3-amino-1,2,4-triazole)-Leu-Lys(isopropyl)-Pro-D-Ala-NH2, where Q1 and Q2 are amino acids, such as Gly, $g(b)-Ala, Ala, D-Ala, Ser, Aib, Ahx and Gab. Examples of other GnRH antagonists include Ac-$g(b)-D-2NAL-(4C1)D-Phe-D-3PAL-Ser-Aph(Atz)-D-Aph(Ac)-Leu-Lys(isopropyl)-Pro-D-Ala-NH2, Ac-$g(b)-D-2NAL-(4C1)D-Phe-D-3PAL-Ser-Aph($g(b)-Ala)(3-amino-1,2,4-triazole)-D-Aph($g(b)-Ala)(3-amino-1,2,4-triazole)-Leu-Lys(isopropyl)-Pro-D-Ala-NH2, Ac-$g(b)-D-2NAL-(4C1)D-Phe-D-3PAL-Ser-Aph(Ac-D-Ser)-D-Aph(Ac-D-Ser)-Leu-Lys(isopropyl)-Pro-D-Ala-NH2, and Ac-$g(b)-D-2NAL-(4C1)D-Phe-D-3PAL-Ser-Aph(Ac)-D-Aph(Ac)-Leu-Lys(isopropyl)-Pro-D-Ala-NH2.(FR) Des analogues du décapeptide anti-gonadolibérine (GnRH) qui comprennent deux acides aminés fortement modifiés en positions 5 et 6 bloquent la sécrétion de gonadotropines par l'hypophyse et bloquent la libération de stéroïdes par les gonades. L'administration d'une dose efficace de ces antagonistes de la GnRH empêche l'ovulation des ÷ufs chez les mammifères femelles et/ou la libération de stéroïdes par les gonades, et peut être utilisée pour traiter des tumeurs stéroïdo-dépendantes. Les peptides particulièrement efficaces, hydrosolubles à un pH physiologique, et qui ont une tendance à se gélifier lorsqu'ils sont administrés in vivo, ont la formule suivante: Ac-$g(b)-D-2NAL-(4Cl)D-Phe-D-3PAL-Ser-Aph(Q1)(3-amino-1,2,4-triazole)-D-Aph(Q2)(3-amino-1,2,4-triazole)-Leu-Lys(isopropyl)-Pro-D-Ala-NH2. Dans cette formule Q1 et Q2 sont des acides aminés tels que Gly, $g(b)-Ala, Ala, D-Ala, Ser, Aib, Ahx et Gab. On notera également d'autres exemples d'antagonistes de la GnRH dont Ac-$g(b)-D-2NAL-(4Cl)D-Phe-D-3PAL-Ser-Aph(Atz)-D-Aph(Ac)-Leu-Lys(isopropyl)-Pro-D-Ala-NH2, le Ac-$g(b)-D-2NAL-(4Cl)D-Phe-D-3PAL-Ser-Aph($g(b)-Ala)(3-amino-1,2,4-triazole)-D-Aph($g(b)-Ala)(3-amino-1,2,4-triazole)-Leu-Lys(isopropyl)-Pro-D-Ala-NH2, le Ac-$g(b)-D-2NAL-(4Cl)D-Phe-D-3PAL-Ser-Aph(Ac-D-Ser)-D-Aph(Ac-D-Ser)-Leu-Lys(isopropyl)-Pro-D-Ala-NH2, et le Ac-$g(b)-D-2NAL-(4Cl)D-Phe-D-3PAL-Ser-Aph(Ac)-D-Aph(Ac)-Leu-Lys(isopropyl)-Pro-D-Ala-NH2.

  这段文本讲述了含有两个在第5和第6位显著改变的氨基酸的GnRH十肽类似物可以抑制垂体腺激素的分泌和抑制生殖腺的类固醇释放。使用有效量的这种GnRH拮抗剂可以预防雌性哺乳动物卵子的排卵和/或生殖腺的类固醇释放，并可用于治疗类固醇依赖性肿瘤。特别有效的肽类在生理pH下水溶性，并且在体内注射时不易凝胶，其公式如下：Ac-$g(b)-D-2NAL-(4C1)D-Phe-D-3PAL-Ser-Aph(Q1)(3-氨基-1,2,4-三唑)-D-Aph(Q2)(3-氨基-1,2,4-三唑)-Leu-Lys(isopropyl)-Pro-D-Ala-NH2，其中Q1和Q2是氨基酸，例如Gly，$g(b)-Ala，Ala，D-Ala，Ser，Aib，Ahx和Gab。其他GnRH拮抗剂的例子包括Ac-$g(b)-D-2NAL-(4C1)D-Phe-D-3PAL-Ser-Aph(Atz)-D-Aph(Ac)-Leu-Lys(isopropyl)-Pro-D-Ala-NH2，Ac-$g(b)-D-2NAL-(4C1)D-Phe-D-3PAL-Ser-Aph($g(b)-Ala)(3-氨基-1,2,4-三唑)-D-Aph($g(b)-Ala)(3-氨基-1,2,4-三唑)-Leu-Lys(isopropyl)-Pro-D-Ala-NH2，Ac-$g(b)-D-2NAL-(4C1)D-Phe-D-3PAL-Ser-Aph(Ac-D-Ser)-D-Aph(Ac-D-Ser)-Leu-Lys(isopropyl)-Pro-D-Ala-NH2，以及Ac-$g(b)-D-2NAL-(4C1)D-Phe-D-3PAL-Ser-Aph(Ac)-D-Aph(Ac)-Leu-Lys(isopropyl)-Pro-D-Ala-NH2。
• Arginine deiminase mutant and methods of using the same
  申请人：Jiangnan University

  公开号：US10557130B2

  公开（公告）日：2020-02-11

  An arginine deiminase mutant with improved enzyme activity and temperature stability and application thereof were provided, belonging to the technical field of genetic engineering and enzyme engineering. The arginine deiminase mutant is proline, namely Gly292 Pro, mutated from glycine near an enzyme active center. A wild-type arginine deiminase arcA coding gene is molecularly modified by a site-directed mutation technique to obtain a mutant enzyme ADIG292P, which has glycine at position 292 of an amino acid sequence of the wild type arginine deiminase mutated to proline. The arginine deiminase, modified by site-directed mutation, of the present invention has 1.5 times of increase in enzyme activity and 5.43 times of increase in half-life period at 40° C. compared with the wild-type enzyme, which solves the problems of low catalytic ability and temperature stability during the catalytic synthesis of citrulline using arginine deiminase, and lays a foundation for industrial production of efficient synthesis of citrulline and medication application.

  本发明提供了一种具有更高酶活性和温度稳定性的精氨酸脱亚胺酶突变体及其应用，属于基因工程和酶工程技术领域。该精氨酸脱氨酶突变体是在酶活性中心附近由甘氨酸突变而来的脯氨酸，即 Gly292 Pro。通过定点突变技术对野生型精氨酸脱氨酶 arcA 编码基因进行分子改造，得到突变体酶 ADIG292P，它将野生型精氨酸脱氨酶氨基酸序列中 292 位的甘氨酸突变为脯氨酸。本发明经定点突变修饰的精氨酸脱亚胺酶与野生型酶相比，酶活性提高了1.5倍，40℃半衰期提高了5.43倍，解决了精氨酸脱亚胺酶催化合成瓜氨酸过程中催化能力低和温度稳定性差的问题，为高效合成瓜氨酸的工业化生产和药物应用奠定了基础。
• Arginine deiminase mutant methods of using the same
  申请人：Jiangnan University

  公开号：US10815470B2

  公开（公告）日：2020-10-27

  An arginine deiminase mutant with improved enzyme activity and temperature stability and application thereof were provided, belonging to the technical field of genetic engineering and enzyme engineering. The arginine deiminase mutant is proline, namely Gly292 Pro, mutated from glycine near an enzyme active center. A wild-type arginine deiminase arcA coding gene is molecularly modified by a site-directed mutation technique to obtain a mutant enzyme ADIG292P, which has glycine at position 292 of an amino acid sequence of the wild type arginine deiminase mutated to proline. The arginine deiminase, modified by site-directed mutation, of the present invention has 1.5 times of increase in enzyme activity and 5.43 times of increase in half-life period at 40° C. compared with the wild-type enzyme, which solves the problems of low catalytic ability and temperature stability during the catalytic synthesis of citrulline using arginine deiminase, and lays a foundation for industrial production of efficient synthesis of citrulline and medication application.

  本发明提供了一种具有更高酶活性和温度稳定性的精氨酸脱亚胺酶突变体及其应用，属于基因工程和酶工程技术领域。该精氨酸脱氨酶突变体是在酶活性中心附近由甘氨酸突变而来的脯氨酸，即 Gly292 Pro。通过定点突变技术对野生型精氨酸脱氨酶 arcA 编码基因进行分子改造，得到突变体酶 ADIG292P，它将野生型精氨酸脱氨酶氨基酸序列中 292 位的甘氨酸突变为脯氨酸。本发明经定点突变修饰的精氨酸脱亚胺酶与野生型酶相比，酶活性提高了1.5倍，40℃半衰期提高了5.43倍，解决了精氨酸脱亚胺酶催化合成瓜氨酸过程中催化能力低和温度稳定性差的问题，为高效合成瓜氨酸的工业化生产和药物应用奠定了基础。
• PARATHYROID HORMONE ANALOGUES MODIFIED AT POSITIONS 3, 6 or 9
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：EP0539491A1

  公开（公告）日：1993-05-05