丁酸觅糖苷 | 116112-82-4

• 物质功能分类: 生物化工 - 生化试剂
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 丁酸觅糖苷
• 英文名称: 3-carboxypropyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
• 英文别名: 4-[[2,3,6-Tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-|A-D-galactopyranosyl)-|A-D-glucopyranosyl]oxy]butanoic acid；4-[(2R,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]oxybutanoic acid
• CAS: 116112-82-4
• 化学式: C₃₀H₄₂O₂₀
• 分子量: 722.651
• InChiKey: NTNRPTIODYMBSL-GFBMDZRWSA-N

物化性质

• 沸点：
  745.0±60.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  50
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  258
• 氢给体数：
  1
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 丁酸觅糖苷 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到succinimidoxycarbonylpropyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of multivalent β-lactosyl clusters as potential tumor metastasis inhibitors

  摘要：

  A beta-lactosyl residue was linked to the amino groUpS Of L-lysyl-L-lysine through spacer arms of three different lengths (C2, C4, and C-9) to give trivalent beta-lactosyl clusters in order to increase the inhibitory activity of the beta-lactosyl group against tumor cell colonization. Thus, O-(2,3,4,6-tetra-0-acetyl-beta-D-galactopyranosyl)-(1 --> 4)-2,3,6-tri-O-acetyl-glucopyranosyl trichloroacetimidate was treated with methyl or benzyl hydroxyethanoate, methyl or benzyl 4-hydroxybutanoate, and methyl 9-hydroxynonanoate, respectively, in the presence of trimethylsilyl trifluoromethanesulfonate to give the corresponding beta-lactosides. These were coupled to L-lysyl-L-lysine, after conversion to the N-hydroxysuccinimide esters, to yield the corresponding trivalent beta-lactosyl-L-lysyl-L-lysine conjugates in good yields. The beta-lactosyl group with a C4 spacer arm was also coupled similarly to poly(L-lysine) (M(r) 3800) to form a polyvalent beta-lactosyl cluster. Coinjection of the trivalent (with C2 and C4 spacer arms) and polyvalent beta-lactosyl clusters with the highly metastatic B16 murine melanoma cells inhibited the formation of lung colonies in C57/BL mice, whereas the trivalent cluster with a C-9 spacer arm displayed no activity.

  DOI：

  10.1016/0008-6215(93)80071-l
• 作为产物：
  描述：

  在 重铬酸吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以43%的产率得到丁酸觅糖苷
  参考文献：
  名称：

  Synthesis and Properties of Neoglycoconjugates Carrying A Dimerization Motif of Glycophorin A Transmembrane Domain

  摘要：

  A new class of glycopeptides 8 and 10, were synthesized from 3-carboxypropyl lactoside 4 and tricosapeptide 6 on a solid support. Their amino acid sequences include a dimerization motif of glycophorin A transmembrane domain. The dimerizable properties of the synthesized glycopeptides and non-glycosylated peptides were investigated by Tris-Tricine-SDS-PAGE.

  DOI：

  10.1080/07328309808002342