2-propenesulfenic acid | 62965-27-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 烯丙基硫化合物
• 英文名称: 2-propenesulfenic acid
• 英文别名: allyl sulphenic acid；Allylsulfenate；3-hydroxysulfanylprop-1-ene
• CAS: 62965-27-9
• 化学式: C₃H₆OS
• 分子量: 90.146
• InChiKey: WLHNIAVMSNXYHO-UHFFFAOYSA-N

物化性质

• 沸点：
  163.3±33.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  5
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-辛炔-3-醇 、 2-propenesulfenic acid 反应 2.5h， 生成 1-(2-methyl-1-oxo-2,3-dihydrothiophen-5-yl)hexan-1-ol 、 (4E)-5-(3-hydroxyoct-1-en-2-ylsulfinyl)undeca-1,4-dien-6-ol
  参考文献：
  名称：

  烯丙磺酸与炔烃的反应生成1-氧噻吩衍生物

  摘要：

  1-炔基亚氨酰基-2-氰基乙烷在炔烃中的热解引发了五个连续的周环反应，从而导致生成了硫醇1-氧化物衍生物。

  DOI：

  10.1016/s0040-4039(00)77863-4
• 作为产物：
  描述：

  大蒜素 生成 2-propenesulfenic acid
  参考文献：
  名称：

  Calvey E. M., Roach J. A. G., Block E., J. Chromatogr. Sci., 32 (1994) N 3, S 93-96

  摘要：

  DOI：

文献信息

• Calvey E. M., Roach J. A. G., Block E., J. Chromatogr. Sci., 32 (1994) N 3, S 93-96
  作者：Calvey E. M., Roach J. A. G., Block E.

  DOI：——

  日期：——
• Purification, characterization, and crystallization of alliinase from garlic
  作者：E. Bartholomeus Kuettner、Rolf Hilgenfeld、Manfred S. Weiss

  DOI：10.1016/s0003-9861(02)00088-7

  日期：2002.6

  Glycosylated dimeric alliinase (EC 4.4.1.4) was purified to homogeneity from its natural source, garlic. With 660 units/mg, the specific enzymatic activity of the pure enzyme is the highest reported to date. Based on both CD spectroscopy data and sequence-derived secondary structure prediction, the alpha-helix content of alliinase was estimated to be about 30%. Comparisons of all available amino acid sequences of alliinases revealed a common cysteine pattern of the type C-x18-19-C-x-C-x2-C-x5-C-x6-C in the N-terminal part of the sequences. This pattern is conserved in alliinases but absent in other pyridoxal 5'-phosphate-dependent enzymes. It suggests the presence of an epidermal growth factor-like domain in the three-dimensional structures of alliinases, making them unique among the various families of pyridoxal 5'-phosphate-dependent enzymes. Well-ordered three-dimensional crystals of garlic alliinase were obtained in four different forms. The best diffraction was observed with crystal form IV (space group P2(1)2(1)2(1), a=68.4, b=101.1, c=155.7 A) grown from an ammonium sulfate solution. These crystals diffract to at least 1.5 A resolution at a synchrotron source and are suitable for structure determination.
• Two Structures of Alliinase from Alliium sativum L.: Apo Form and Ternary Complex with Aminoacrylate Reaction Intermediate Covalently Bound to the PLP Cofactor
  作者：Linda J.W. Shimon、Aharon Rabinkov、Irina Shin、Talia Miron、David Mirelman、Meir Wilchek、Felix Frolow

  DOI：10.1016/j.jmb.2006.11.041

  日期：2007.2

  Alliinase (alliin lyase EC 4.4.1.4), a PLP-dependent alpha, beta-eliminating lyase, constitutes one of the major protein components of garlic (Alliium sativum L.) bulbs. The enzyme is a homodimeric glycoprotein and catalyzes the conversion of a specific non-protein sulfur-containing amino acid alliin ((+S)-allyl-L-cysteine sulfoxide) to allicin (diallyl thiosulfinate, the well known biologically active component of freshly crushed garlic), pyruvate and ammonia. The enzyme was crystallized in the presence of (+S)-allyl-L-cysteine, forming dendrite-like monoclinic crystals. In addition, intentionally produced apo-enzyme was crystallized in tetragonal form. These structures of alliinase with associated glycans were resolved to 1.4 A and 1.61 A by molecular replacement. Branched hexasaccharide chains N-linked to Asn146 and trisaccharide chains N-linked to Asn328 are seen. The structure of hexasaccharide was found similar to "short chain complex vacuole type" oligosaccharide most commonly seen in plant glycoproteins. An unexpected state of the enzyme active site has been observed in the present structure. The electron density in the region of the cofactor made it possible to identify the cofactor moiety as aminoacrylate intermediate covalently bound to the PLP cofactor. It was found in the present structure to be stabilized by large number of interactions with surrounding protein residues. Moreover, the existence of the expected internal aldimine bond between the epsilon-amino group of Lys251 and the aldehyde of the PLP is ruled out on the basis of a distinct separation of electron density of Lys251. The structure of the active site cavity in the apo-form is nearly identical to that seen in the holo-form, with two sulfate ions, an acetate and several water molecules from crystallization conditions that replace and mimic the PLP cofactor.
• Reaction of allylsulphenic acid with alkynes to give thiolan 1-oxide derivatives
  作者：Richard Bell、Peter D. Cottam、John Davies、D.Neville Jones、Nicholas A. Meanwell

  DOI：10.1016/s0040-4039(00)77863-4

  日期：1980.1

  Thermolysis of 1-allylsulphinyl-2-cyanoethane in alkynes initiated five consecutive pericyclic reactions which led to the formation of thiolan 1-oxide derivatives.

  1-炔基亚氨酰基-2-氰基乙烷在炔烃中的热解引发了五个连续的周环反应，从而导致生成了硫醇1-氧化物衍生物。