β-D-galactopyranosyl β-D-glucopyranoside | 96480-23-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-galactopyranosyl β-D-glucopyranoside
• 英文别名: Glc(b1-1b)Gal；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-3,4,5-triol
• CAS: 96480-23-8
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: HDTRYLNUVZCQOY-PSWXTKDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 在 sodium methylate 、 氰化汞 作用下， 以 甲醇 、 硝基甲烷 为溶剂， 生成 β-D-galactopyranosyl β-D-glucopyranoside
  参考文献：
  名称：

  Selectivity and efficiency of utilization of galactosyl-oligosaccharides by bifidobacteria.

  摘要：

  合成了新半乳糖双糖（α-D-半乳糖吡喃苷 β-D-半乳糖吡喃苷）、β-D-半乳糖吡喃苷 β-D-葡萄糖吡喃苷、β-D-半乳糖吡喃苷 α-D-葡萄糖吡喃苷、α-D-半乳糖吡喃苷 β-D-葡萄糖吡喃苷（GII）和α-D-半乳糖吡喃苷 β-D-果糖呋喃苷（2→6）-β-D-果糖呋喃苷（Gf），作为可能选择性和高效增强人类肠道双歧杆菌生长的糖源。Gf 是通过使用左旋糖酶合成的，其他糖则通过科尼希斯-克诺尔反应合成。通过酶水解确认了这些糖的结构。所有测试的双歧杆菌菌株几乎均有效利用了这些糖。其中，GII、Gf 和美洲蓟糖不被嗜酸乳杆菌或粪链球菌利用，仅被少数肠杆菌科的菌株利用（相当于乳糖蔗糖）。此外，在双歧杆菌细胞的生长活性和细胞代生时间方面，这三种糖的效果实际上与乳糖或乳糖蔗糖相当有效。

  DOI：

  10.1248/cpb.33.710

文献信息

• The use of O-glycosyl trichloroacetimidates in the synthesis of unsymmetrical trehalose analogues
  作者：Tor E.C.L. Ronnow、Morten Meldal、Klaus Bock

  DOI：10.1016/s0957-4166(00)86287-4

  日期：1994.11

  The coupling of O-glycosyltrichloroacetimidates with 2,3,4,6-tetra-O-benzylated monosaccharides (gluco, manno, galacto) promoted by TMSOTf is described, and the compositions of the crude reaction mixtures, determined by C-13 NMR spectroscopy, are presented. Unsymmetrical trehalose derivatives can be synthesized by such couplings. The versatility of the trichloroacetimidates for the synthesis of trehalose analogues has furthermore been demonstrated by the glycosylation of anomerically unprotected maltose heptabenzoylate affording two trehalose-containing trisaccharides, and by the synthesis of alpha-D-galactopyranosyl alpha-D-mannopyranoside.
• US5098588A
  申请人：——

  公开号：US5098588A

  公开（公告）日：1992-03-24
• [EN] MULTIVALENT MIMETICS AND PEPTIDE MIMETICS FOR BLOCKING CARBOHYDRATE-DEPENDENT CELLULAR INTERACTION AND FOR ELICITING ANTICARBOHYDRATE T-CELL RESPONSE<br/>[FR] SUBSTANCES MIMETIQUES POLYVALENTES ET SUBSTANCES MIMETIQUES PEPTIDIQUES DESTINEES A BLOQUER L'INTERACTION CELLULAIRE DEPENDANT DE L'HYDRATE DE CARBONE ET A PROVOQUER LA REPONSE ANTI-HYDRATE DE CARBONE DES LYMPHOCYTES T
  申请人：——

  公开号：WO1993023031A1

  公开（公告）日：1993-11-25

  [EN] A stabilized carbohydrate epitope having more resistance to metabolic degradation than a corresponding naturally occurring carbohydrate epitope, or those assembled in multivalent structures. A mimetic of a carbohydrate epitope, wherein said mimetic has a structure such that the mimetic has about the same or higher antibody-binding or selectin-binding activities, immunogenicity and antigenicity as that of a corresponding naturally occurring carbohydrate epitope. A process for preparing the above-described mimetic of a carbohydrate epitope is described as well as medicaments and methods for inhibiting carbohydrate-mediated cell adhesion and a vaccine and method of vaccinating to induce an anti-carbohydrate T cell response.
  [FR] Epitope d'hydrate de carbone stabilisé présentant une résistance plus grande à la dégradation métabolique qu'un épitope d'hydrate de carbone naturel correspondant, ou que ceux assemblés dans des structures polyvalentes. Substance mimétique relative à un épitope d'hydrate de carbone, cette substance présentant une structure telle qu'elle présente des activités de liaison d'anticorps ou de la sélectine et une immunogénicité et une antigénicité pratiquement égales ou supérieures à celles d'un épitope d'hydrate de carbone naturel correspondant. On décrit un procédé de préparation de la substance mimétique relative à un épitope d'hydrate de carbone mentionnée ci-dessus, ainsi que les médicaments et les procédés de blocage d'adhésion cellulaire induite par l'hydrate de carbone, et un vaccin et une méthode de vaccination pour induire une réponse anti-hydrate de carbone des lymphocytes T.
• Selectivity and efficiency of utilization of galactosyl-oligosaccharides by bifidobacteria.
  作者：YOSHIHIRO MINAMI、KOUHEI YAZAWA、KUMIKO NAKAMURA、ZENZO TAMURA

  DOI：10.1248/cpb.33.710

  日期：——

  Neogalactobiose (α-D-galactopyranosyl β-D-galactopyranoside), β-D-galactopyranosyl β-D-glucopyranoside, β-D-galactopyranosyl α-D-glucopyranoside, α-D-galactopyranosyl β-D-glucopyranoside (GII), and α-D-galactopyranosyl β-D-fructofuranosyl-(2→6)-β-D-fructofuranoside (Gf) were synthesized as sugar sources which might selectively and efficiently enhance the growth of bifidobacteria in the human intestines. Gf was synthesized by using levansucrase and the others by means of the Koenigs-Knorr reaction. The structures of these sugars were confirmed by enzymic hydrolysis. All of these sugars were utilized by almost all strains of Bifidobacterium tested. Among them, GII, Gf and stachyose were not utilized by Lactobacillus acidophilus or Streptococcus faecalis, and were utilized by only a few strains of Enterobacteriaceae (comparable to lactosucrose). Furthermore, as regards both the growth activity of bifidobacterial cells and the generation time of the cells, the three sugars were virtually as effective as lactose or lactosucrose.

  合成了新半乳糖双糖（α-D-半乳糖吡喃苷 β-D-半乳糖吡喃苷）、β-D-半乳糖吡喃苷 β-D-葡萄糖吡喃苷、β-D-半乳糖吡喃苷 α-D-葡萄糖吡喃苷、α-D-半乳糖吡喃苷 β-D-葡萄糖吡喃苷（GII）和α-D-半乳糖吡喃苷 β-D-果糖呋喃苷（2→6）-β-D-果糖呋喃苷（Gf），作为可能选择性和高效增强人类肠道双歧杆菌生长的糖源。Gf 是通过使用左旋糖酶合成的，其他糖则通过科尼希斯-克诺尔反应合成。通过酶水解确认了这些糖的结构。所有测试的双歧杆菌菌株几乎均有效利用了这些糖。其中，GII、Gf 和美洲蓟糖不被嗜酸乳杆菌或粪链球菌利用，仅被少数肠杆菌科的菌株利用（相当于乳糖蔗糖）。此外，在双歧杆菌细胞的生长活性和细胞代生时间方面，这三种糖的效果实际上与乳糖或乳糖蔗糖相当有效。