O-α-D-galactopyranosyl-(1->3)-O-α-D-glucopyranosyl-(1->2)-β-D-fructofuranoside | 2650-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-α-D-galactopyranosyl-(1->3)-O-α-D-glucopyranosyl-(1->2)-β-D-fructofuranoside
• 英文别名: α-D-Galactopyranosyl(-1,3)-α,D-glucopyranosyl-(1,2)-β-D-fructofuranosid；Loliose；(2R,3R,4S,5R,6R)-2-[(2R,3R,4S,5R,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 2650-46-6
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: AEVXMUQAEMWBMR-ZRQHEJPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  269
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  蔗糖 、 uridine 5'-(α-D-galactopyranosyl diphosphate) 生成 氢(+1)阳离子 、 O-α-D-galactopyranosyl-(1->3)-O-α-D-glucopyranosyl-(1->2)-β-D-fructofuranoside 、 UDP
  参考文献：
  名称：

  Fructans, But Not the Sucrosyl-Galactosides, Raffinose and Loliose, Are Affected by Drought Stress in Perennial Ryegrass

  摘要：

  本研究的目的是评估蔓延性黑麦草中蔗糖-半乳糖苷（loliose [α-d-Gal（1,3）α-d-Glc（1,2）β-d-Fru]和蔗糖蜜（raffinose [α-d-Gal（1,6）α-d-Glc（1,2）β-d-Fru]）在耐旱性中的潜在作用，并将其与果聚糖进行比较。为此，首先建立了loliolse生物合成途径，并通过UDP-Gal：蔗糖（Suc）3-半乳糖基转移酶（暂定为loliolse合成酶）进行了操作。干旱胁迫既未增加loliolse和raffinose的浓度，也未增加loliolse合成酶和raffinose合成酶（EC 2.4.1.82）的活性。此外，蔗糖蜜的前体物质myoinositol和galactinol的浓度以及myoinositol 1-phosphate synthase（EC 5.5.1.4）和galactinol synthase（EC 2.4.1.123）的基因表达在干旱胁迫下要么降低，要么不受影响。综上所述，这些数据不支持蔓延性黑麦草在营养生长阶段中蔗糖-半乳糖苷在耐旱性中的显然作用。相反，干旱胁迫导致果聚糖在叶组织中积累，主要在叶鞘和伸长叶基部。这种增加主要是由于长链果聚糖（聚合度> 8）的积累，而不伴随蔗糖的增加。有趣的是，干旱胁迫导致根中蔗糖浓度大幅增加，而不是果聚糖浓度。讨论了果聚糖和蔗糖-半乳糖苷在应对胁迫方面的潜在作用。

  DOI：

  10.1104/pp.103.022335

文献信息

• Mitsutomi, Masaru; Ohtakara, Akira, Agricultural and Biological Chemistry, 1988, vol. 52, # 9, p. 2305 - 2312
  作者：Mitsutomi, Masaru、Ohtakara, Akira

  DOI：——

  日期：——
• Fructans, But Not the Sucrosyl-Galactosides, Raffinose and Loliose, Are Affected by Drought Stress in Perennial Ryegrass
  作者：Véronique Amiard、Annette Morvan-Bertrand、Jean-Pierre Billard、Claude Huault、Felix Keller、Marie-Pascale Prud'homme

  DOI：10.1104/pp.103.022335

  日期：2003.8.1

  The aim of this study was to evaluate the putative role of the sucrosyl-galactosides, loliose [α-d-Gal (1,3) α-d-Glc (1,2) β-d-Fru] and raffinose [α-d-Gal (1,6) α-d-Glc (1,2) β-d-Fru], in drought tolerance of perennial ryegrass and to compare it with that of fructans. To that end, the loliose biosynthetic pathway was first established and shown to operate by a UDP-Gal: sucrose (Suc) 3-galactosyltransferase, tentatively termed loliose synthase. Drought stress increased neither the concentrations of loliose and raffinose nor the activities of loliose synthase and raffinose synthase (EC 2.4.1.82). Moreover, the concentrations of the raffinose precursors, myoinositol and galactinol, as well as the gene expressions of myoinositol 1-phosphate synthase (EC 5.5.1.4) and galactinol synthase (EC 2.4.1.123) were either decreased or unaffected by drought stress. Taken together, these data are not in favor of an obvious role of sucrosyl-galactosides in drought tolerance of perennial ryegrass at the vegetative stage. By contrast, drought stress caused fructans to accumulate in leaf tissues, mainly in leaf sheaths and elongating leaf bases. This increase was mainly due to the accumulation of long-chain fructans (degree of polymerization > 8) and was not accompanied by a Suc increase. Interestingly, Suc but not fructan concentrations greatly increased in drought-stressed roots. Putative roles of fructans and sucrosyl-galactosides are discussed in relation to the acquisition of stress tolerance.

  本研究的目的是评估蔓延性黑麦草中蔗糖-半乳糖苷（loliose [α-d-Gal（1,3）α-d-Glc（1,2）β-d-Fru]和蔗糖蜜（raffinose [α-d-Gal（1,6）α-d-Glc（1,2）β-d-Fru]）在耐旱性中的潜在作用，并将其与果聚糖进行比较。为此，首先建立了loliolse生物合成途径，并通过UDP-Gal：蔗糖（Suc）3-半乳糖基转移酶（暂定为loliolse合成酶）进行了操作。干旱胁迫既未增加loliolse和raffinose的浓度，也未增加loliolse合成酶和raffinose合成酶（EC 2.4.1.82）的活性。此外，蔗糖蜜的前体物质myoinositol和galactinol的浓度以及myoinositol 1-phosphate synthase（EC 5.5.1.4）和galactinol synthase（EC 2.4.1.123）的基因表达在干旱胁迫下要么降低，要么不受影响。综上所述，这些数据不支持蔓延性黑麦草在营养生长阶段中蔗糖-半乳糖苷在耐旱性中的显然作用。相反，干旱胁迫导致果聚糖在叶组织中积累，主要在叶鞘和伸长叶基部。这种增加主要是由于长链果聚糖（聚合度> 8）的积累，而不伴随蔗糖的增加。有趣的是，干旱胁迫导致根中蔗糖浓度大幅增加，而不是果聚糖浓度。讨论了果聚糖和蔗糖-半乳糖苷在应对胁迫方面的潜在作用。