O-丙基-D-丝氨酸 | 1021177-37-6

• 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: O-丙基-D-丝氨酸
• 英文名称: O-propyl-D-serine
• 英文别名: propyl (2R)-2-amino-3-hydroxypropanoate
• CAS: 1021177-37-6
• 化学式: C₆H₁₃NO₃
• 分子量: 147.174
• InChiKey: VZNRCOQNPQNNKI-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-丙基-D-丝氨酸 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-propyl aziridine-2-carboxylate
  参考文献：
  名称：

  Chemoselective Peptidomimetic Ligation Using Thioacid Peptides and Aziridine Templates

  摘要：

  Chemoselective peptidomimetic ligation has been made possible using thioacid peptides and NH aziridine-terminated amino acids and peptides. In the course of this reaction, a reduced amide bond is incorporated into the backbone of a peptide. This process enables incorporation of reduced cysteine, reduced substituted cysteine, reduced phenylalanine, and reduced alanine. Our method should be adaptable to other unnatural amino acid residues at the ligation site. Experiments aimed at evaluating the chemoselectivity of this process in the presence of competing thiol nucleophiles suggest high specificity at micromolar concentrations. This holds even in the presence of glutathione, which neutralizes xenobiotic electrophiles in cells.

  DOI：

  10.1021/ja104488d
• 作为产物：
  描述：

  丙醇 、 D-丝氨酸 在 氯化亚砜 、 ammonium hydroxide 、 水 作用下， 反应 48.0h， 生成 O-丙基-D-丝氨酸
  参考文献：
  名称：

  Chemoselective Peptidomimetic Ligation Using Thioacid Peptides and Aziridine Templates

  摘要：

  Chemoselective peptidomimetic ligation has been made possible using thioacid peptides and NH aziridine-terminated amino acids and peptides. In the course of this reaction, a reduced amide bond is incorporated into the backbone of a peptide. This process enables incorporation of reduced cysteine, reduced substituted cysteine, reduced phenylalanine, and reduced alanine. Our method should be adaptable to other unnatural amino acid residues at the ligation site. Experiments aimed at evaluating the chemoselectivity of this process in the presence of competing thiol nucleophiles suggest high specificity at micromolar concentrations. This holds even in the presence of glutathione, which neutralizes xenobiotic electrophiles in cells.

  DOI：

  10.1021/ja104488d

文献信息

• Hydroxamic acid derivative
  申请人：Yamanouchi Pharmaceutical Co., Ltd.

  公开号：US05442110A1

  公开（公告）日：1995-08-15

  ##STR1## A compound represented by general formula (I), a pharmaceutical composition containing same, a process for the production thereof, and an intermediate therefor. In formula (I) R.sup.1 represents lower alkyl which may be substituted by a substituent selected from the group consisting of mercapto, lower alkylthio, arylthio and lower acylthio; R.sup.2, R.sup.3 and R.sup.4 may be the same or different from one another and each represents lower alkyl; X represents oxygen or sulfur; and Y represents a single bond or lower alkylene. The compound (I) has a matrix metalloprotease inhibitory activity and is useful for preventing and treating diseases caused by the progress of connective tissue breakage.

  化合物的通式(I)，包含该化合物的制药组合物，其制备方法以及中间体。在式(I)中，R.sup.1代表可以被来自汞、低级烷基硫、芳基硫和低级酰基硫的取代基取代的低级烷基；R.sup.2、R.sup.3和R.sup.4可以相同，也可以不同，且每个都代表低级烷基；X代表氧或硫；Y代表单键或低级烷基。该化合物(I)具有基质金属蛋白酶抑制活性，可用于预防和治疗由于结缔组织断裂进展而引起的疾病。
• OPTICALLY ACTIVE BISOXAZOLINE COMPOUND, ASYMMETRIC CATALYST, AND METHOD FOR PRODUCING OPTICALLY ACTIVE CYCLOPROPANE COMPOUND USING SAID CATALYST
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2781522A1

  公开（公告）日：2014-09-24

  An optically active bisoxazoline compound represented by formula (1): wherein R1, R2 and R3 each independently represent an alkyl group having 1 to 8 carbon atoms, a phenyl group or a benzyl group, n represents an integer of 0 to 3 and * represents an asymmetric center.

  由式 (1) 代表的光学活性双噁唑啉化合物： 其中 R1、R2 和 R3 各自独立地代表具有 1 至 8 个碳原子的烷基、苯基或苄基，n 代表 0 至 3 的整数，* 代表不对称中心。
• Epimerization- and Protecting-Group-Free Synthesis of Peptidomimetic Conjugates from Amphoteric Amino Aldehydes
  作者：Xinghan Li、Andrei K. Yudin

  DOI：10.1021/ja076155p

  日期：2007.11.1

  We have developed a novel protecting-group-free strategy for the synthesis of peptidomimetic conjugates. The high degrees of stereocontrol and chemoselectivity achieved in this chemistry hinge upon unusual preferences of the amphoteric amino aldehydes. The resulting conjugates contain reduced amide bonds at defined positions, offering a possibility for peptidomimetic ligation. These findings should allow access to templates for introducing both natural and unnatural amino acid residues in close proximity to the reduced amide bond isosteres.
• Chemoselective Peptidomimetic Ligation Using Thioacid Peptides and Aziridine Templates
  作者：Naila Assem、Aditya Natarajan、Andrei K. Yudin

  DOI：10.1021/ja104488d

  日期：2010.8.18

  Chemoselective peptidomimetic ligation has been made possible using thioacid peptides and NH aziridine-terminated amino acids and peptides. In the course of this reaction, a reduced amide bond is incorporated into the backbone of a peptide. This process enables incorporation of reduced cysteine, reduced substituted cysteine, reduced phenylalanine, and reduced alanine. Our method should be adaptable to other unnatural amino acid residues at the ligation site. Experiments aimed at evaluating the chemoselectivity of this process in the presence of competing thiol nucleophiles suggest high specificity at micromolar concentrations. This holds even in the presence of glutathione, which neutralizes xenobiotic electrophiles in cells.