o,o'-diiodo-1,1'-dimyristoyl-2,2'-<11,11'-bisundecanoyl>-sn-glycero-3-phosphocholine | 164936-98-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油磷脂
• 英文名称: o,o'-diiodo-1,1'-dimyristoyl-2,2'-<11,11'-bisundecanoyl>-sn-glycero-3-phosphocholine
• CAS: 164936-98-5
• 化学式: C₇₉H₁₃₆I₂N₂O₁₉P₂
• 分子量: 1733.71
• InChiKey: YGFIUOQERFECKV-FAECOVEHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.63
• 重原子数：
  104.0
• 可旋转键数：
  70.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  257.91
• 氢给体数：
  0.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  o,o'-diiodo-1,1'-dimyristoyl-2,2'-<11,11'-bisundecanoyl>-sn-glycero-3-phosphocholine 在 palladium on activated charcoal 氢气 、 sodium acetate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 以84%的产率得到1,1'-dimyristoyl-2,2'-<11,11'-bisundecanoyl>-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  Yamamoto, Masakuni; Dolle, Valerie; Warnock, William, Bulletin de la Societe Chimique de France, 1994, vol. 131, # 3, p. 317 - 329

  摘要：

  DOI：
• 作为产物：
  描述：

  CdCl2 complex of lysomyristoylphosphatidylcholine 、 o,o'-diiodo-3,3'-(11,11'-bisundecanoyl)bis(thiazolidine-2-thione) 在 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 以55%的产率得到o,o'-diiodo-1,1'-dimyristoyl-2,2'-<11,11'-bisundecanoyl>-sn-glycero-3-phosphocholine
  参考文献：
  名称：

  Yamamoto, Masakuni; Dolle, Valerie; Warnock, William, Bulletin de la Societe Chimique de France, 1994, vol. 131, # 3, p. 317 - 329

  摘要：

  DOI：

文献信息

• Regioselective Photolabeling of Glycophorin A in Membranes
  作者：Yoshikatsu Ogawa、Wolfgang Hahn、Philippe Garnier、Nobuaki Higashi、Dominique Massotte、Marie-Hélène Metz-Boutigue、Bernard Rousseau、Masato Kodaka、Junzo Sunamoto、Guy Ourisson、Yoichi Nakatani

  DOI：10.1002/1521-3765(20020415)8:8<1843::aid-chem1843>3.0.co;2-a

  日期：2002.4.15

  We have developed a chemical method for directly identifying the amino acid residues of the transmembrane domain of a protein that are located right in the center of the membrane. Glycophorin A (GPA), the major sialoglycoprotein of human erythrocytes. was the first membrane protein whose primary sequence was elucidated, but its three-dimensional structure is still not known. GPA has been reconstituted into liposomes formed from dimyristoylphosphatidylcholine, dimyristoylphosphatidylserine, cholesterol, and a bola-amphiphilic phospholipidic photoactivatable probe (radioactive probe 1) by a detergent-mediated method. Electron microscopy confirmed the formation of spherical vesicular structures, and sucrose-density gradients revealed that the proteoliposomes comprised only one membrane fraction. Proteinase-K digestion of GPA in the proteoliposomes suggested that the orientation of GPA in reconstituted proteoliposomes was virtually identical to that observed in natural erythrocyte membranes. After photo-irradiation of the reconstituted proteoliposomes and in situ tryptic digestion, the photolabeled amino acid residues were analyzed by Edman degradation and their radioactivity was measured. Val80 and Met81, which had been assumed to be located near the center of the transmembrane domain of GPA, were indeed highly selectively photolabeled by probe 1. The new method might be applied to analyze the three-dimensional arrangement of the transmembrane domain of protein complexes that are made up from several subunits.
• Mid-Membrane Photolabeling of the Transmembrane Domain of Glycophorin A in Phospholipid Vesicles
  作者：Yoshikatsu Ogawa、Wolfgang Hahn、Philippe Garnier、Nobuaki Higashi、Dominique Massotte、Marie-Hélène Metz-Boutigue、Bernard Rousseau、Junzo Sunamoto、Guy Ourisson、Yoichi Nakatani

  DOI：10.1002/1521-3773(20010302)40:5<944::aid-anie944>3.0.co;2-o

  日期：2001.3.2

  The tandem use of the photosensitive bola-amphiphile 1 (X=3 H) and cholesterol enabled the determination of the center of the transmembrane domain of glycophorin A (131 amino acid residues) in a membrane by selective functionalization of the protein within a phospholipid bilayer.