3-O-α-D-galactopyranosyl-D-galactose | 7313-98-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-O-α-D-galactopyranosyl-D-galactose
• 英文别名: alpha-D-galactosyl-(1->3)-D-galactose；(3R,4S,5S,6R)-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2,3,5-triol
• CAS: 7313-98-6
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: QIGJYVCQYDKYDW-SDOYDPJRSA-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

• 作为反应物：
  描述：

  3-O-α-D-galactopyranosyl-D-galactose 生成 (3R,4S,5S,6R)-3,5-Dimethoxy-6-methoxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-ol
  参考文献：
  名称：

  Structural investigation of Klebsiella serotype K46 poly-saccharide

  摘要：

  The structure of the capsular polysaccharide from Klebsiella type K46 has been investigated by using the techniques of methylation analysis, periodate oxidation, and partial hydrolysis. The anomeric linkages were determined by 1H- and 13C-n.m.r. spectroscopy of the polysaccharide and of derived poly- and oligo-saccharides obtained through degradative procedures. 1H-N.m.r. spectroscopy of the polysaccharide in D2O showed clearly a ratio of one (1-carboxyethylidene) group (CH3, delta 1.47) to six anomeric protons (delta 4.62--5.29). The polysaccharide was shown to consist of the following hexasaccharide repeating unit, which is unique in this series in having a (1-carboxyethylidene) acetal group on a lateral, but nonterminal, sugar residue. (Formula: see text).

  DOI：

  10.1016/s0008-6215(00)85903-0
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 palladium on activated charcoal 四丁基溴化铵 、 氢气 、 4-甲基苯磺酸吡啶 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 、 三氟乙酸 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 74.5h， 生成 3-O-α-D-galactopyranosyl-D-galactose
  参考文献：
  名称：

  Practical Synthesis of the Disaccharide Epitope,D-Galactopyranosyl-α-1,3-D- galactopyranose, by using 1,2;5,6-Di-O-cyclohexylidene-α-D-galactofuranose as the Glycosyl Acceptor

  摘要：

  D-吡喃半乳糖基-α-1,3-D-吡喃半乳糖（1）通过苯基2,3,4,6-四-O-苄基-1-硫代-β-D-吡喃半乳糖苷（5）或2,3,4,6-四-O-苄基-α-D-吡喃半乳糖基溴化物（8）与1,2:5,6-二-O-环己烯基-α-D-呋喃半乳糖（3）的耦合反应制备，随后对所得保护的α-1,3-二糖进行去-O-苄基化和去-O-环己烯基化，产率良好。

  DOI：

  10.1271/bbb.64.1974

文献信息

• Reverse Reaction of<i>Aspergillus niger</i>APC-9319 α-Galactosidase in a Supersaturated Substrate Solution: Production of α-Linked Galactooligosaccharide (α-GOS)
  作者：Akiko YAMASHITA、Hiroyuki HASHIMOTO、Koki FUJITA、Masamichi OKADA、Shigeharu MORI、Sumio KITAHATA

  DOI：10.1271/bbb.69.1381

  日期：2005.1

  The α-galactosidase that effectively catalyzes a reverse reaction of galactose, Aspergillus niger APC-9319 α-galactosidase, was screened from industrial enzyme preparations for food processing containing α-galactosidase activity. Reverse reaction of A. niger APC-9319 α-galactosidase was performed using a supersaturated solution (90% galactose [w/v]). A. niger APC-9319 α-galactosidase was not inhibited even in high substrate concentration, and effectively catalyzed the reverse reaction. The yield of the reaction product, α-linked galactooligosaccharide (α-GOS), increased greatly as the initial concentration of galactose increased to 90% (w/v), and was more than 50%. Furthermore, the half life of enzyme activity was about three times as long as that using 60% galactose (w/v). α-GOS (1.4 g) was prepared from galactose (3.0 g) by reverse reaction of A. niger APC-9319 α-galactosidase. The α-GOS contained 58% α-galactobiose (α-Gal2), 28% α-galactotriose, and 14% oligosaccharides larger than α-galactotriose. The main component of positional isomers in α-Gal2 was α-1,6Gal2.

  从含有α-半乳糖苷酶活性的食品加工工业酶制剂中筛选出能有效催化半乳糖逆反应的Aspergillus niger APC-9319 α-半乳糖苷酶。使用过饱和溶液（90%半乳糖[w/v]）进行A. niger APC-9319 α-半乳糖苷酶的逆反应。即使在高的底物浓度下，A. niger APC-9319 α-半乳糖苷酶也没有被抑制，并且能有效催化逆反应。反应产物α-半乳糖寡糖（α-GOS）的产率随着半乳糖初始浓度的增加而大幅增加，达到90%（w/v）时超过50%。此外，酶活性的半衰期约为使用60%半乳糖（w/v）时的三倍。通过A. niger APC-9319 α-半乳糖苷酶的逆反应，从3.0 g半乳糖制备了1.4 g的α-GOS。α-GOS含有58%的α-半乳二糖（α-Gal2），28%的α-半乳三糖，以及14%的大于α-半乳三糖的寡糖。α-Gal2中的主要位置异构体是α-1,6Gal2。
• Methods for synthesis of alpha-d-gal (1~>3) gal-containing oligosaccharides
  申请人：——

  公开号：US20040058888A1

  公开（公告）日：2004-03-25

  This invention relates to reagents and methods for synthesis of biologically active di- and tri-saccharides comprising &agr;-D-Gal(1→3)-D-Gal. In particular the invention provides novel reagents, intermediates and processes for the solution or solid phase synthesis of &agr;-D-galactopyranosyl-(1→3)-D-galactose, and derivatives thereof. In one preferred embodiments the invention provides a protected monosaccharide building block of general formula (II): in which R 3 is methoxy or methyl; R 1 is H, benzoyl, pivaloyl, 4-chlorobenzoyl, acetyl, chloroacetyl, levulinoyl, 4-methylbenzoyl, benzyl, 3,4-methylenedioxybenzyl, 4-methoxybenzyl, 4-chlorobenzyl, 4-acetamidobenzyl, or 4-azidobenzyl; and R 2 is H, Fmoc, benzoyl, pivaloyl, 4-chlorobenzoyl, acetyl, chloroacetyl, levulinoyl, 4-methylbenzoyl, benzyl, 3,4-methylenedioxybenzyl, 4-methoxybenzyl, 4 -chlorobenzyl, 4-acetamidobenzyl, or 4-azidobenzyl. 1

  本发明涉及用于合成具有生物活性的二糖和三糖的试剂和方法，这些糖包括α-D-Gal(1→3)-D-Gal。特别地，本发明提供了用于溶液或固相合成α-D-半乳糖基-(1→3)-D-半乳糖及其衍生物的新试剂、中间体和工艺。在一个优选的实施例中，本发明提供了一种保护的单糖构建块，其通式为(II)：其中R3是甲氧基或甲基；R1是H、苯甲酰基、特戊酰基、4-氯苯甲酰基、乙酰基、氯乙酰基、乙酰乙酰基、4-甲基苯甲酰基、苄基、3,4-亚甲二氧基苄基、4-甲氧基苄基、4-氯苄基、4-乙酰氨基苄基或4-叠氮苄基；R2是H、芴甲氧羰基(Fmoc)、苯甲酰基、特戊酰基、4-氯苯甲酰基、乙酰基、氯乙酰基、乙酰乙酰基、4-甲基苯甲酰基、苄基、3,4-亚甲二氧基苄基、4-甲氧基苄基、4-氯苄基、4-乙酰氨基苄基或4-叠氮苄基。
• Enhanced immunogenicity of tumor associated antigens by addition of alphaGal epitopes
  申请人：Mautino Mario R.

  公开号：US20090060930A1

  公开（公告）日：2009-03-05

  The invention relates to methods and compositions for causing the selective targeting and killing of tumor cells. The present invention describes prophylactic or therapeutic cancer vaccines based on purified TAA proteins or TAA-derived synthetic peptides altered by chemical, enzymatic or chemo-enzymatic methods to introduce αGal epitopes or αGal glycomimetic epitopes, in order to allow for enhanced opsonization of the antigen by natural anti-αGal antibodies to stimulate TAA capture and presentation, thereby inducing a humoral and cellular immune response to the TAA expressed by a tumor. The animal's immune system thus is stimulated to produce tumor specific cytotoxic cells and antibodies which will attack and kill tumor cells present in the animal.

  本发明涉及用于选择性靶向和杀灭肿瘤细胞的方法和组合物。本发明描述了基于纯化的TAA蛋白或经化学、酶或化酶改变的TAA衍生合成肽的预防或治疗癌症疫苗，以引入αGal表位或αGal糖类似表位，以增强天然抗αGal抗体对抗原的包覆作用，刺激TAA的捕获和呈递，从而诱导针对肿瘤表达的TAA的体液和细胞免疫反应。动物的免疫系统因此被激发产生肿瘤特异性细胞毒性细胞和抗体，攻击和杀灭动物体内存在的肿瘤细胞。
• ENHANCED IMMUNOGENICITY OF TUMOR ASSOCIATED ANTIGENS BY ADDITION OF ALPHAGAL EPITOPES
  申请人：MAUTINO Mario R.

  公开号：US20120003251A1

  公开（公告）日：2012-01-05

  The invention relates to methods and compositions for causing the selective targeting and killing of tumor cells. The present invention describes prophylactic or therapeutic cancer vaccines based on purified TAA proteins or TAA-derived synthetic peptides altered by chemical, enzymatic or chemo-enzymatic methods to introduce αGal epi topes or αGal glycomimetic epitopes, in order to allow for enhanced opsonization of the antigen by natural anti-αGal antibodies to stimulate TAA capture and presentation, thereby inducing a humoral and cellular immune response to the TAA expressed by a tumor. The animal's immune system thus is stimulated to produce tumor specific cytotoxic cells and antibodies which will attack and kill tumor cells present in the animal.

  本发明涉及用于选择性靶向和杀死肿瘤细胞的方法和组合物。本发明描述了基于纯化的TAA蛋白或经化学、酶或化酶改变的TAA衍生合成肽的预防性或治疗性癌症疫苗，以引入αGal表位或αGal糖类模拟表位，从而通过天然抗-αGal抗体增强抗原的包被作用，促进TAA的捕获和呈递，从而诱导对肿瘤细胞表达的TAA的体液和细胞免疫反应。动物的免疫系统因此被刺激产生特异性的肿瘤细胞毒性细胞和抗体，这些细胞和抗体将攻击和杀死动物体内存在的肿瘤细胞。
• Methods and reagents for prevention and/or treatment of infection
  申请人：Institut d'Investigació Biomèdica de Bellvitge (IDIBELL)

  公开号：EP2987503A1

  公开（公告）日：2016-02-24

  The present invention relates to the field of therapeutics and, more in particular, to agents and compositions for the prevention and/or treatment of infection caused by bacteria of the gastrointestinal tract in a subject, said agents and compositions being based on agents comprising a terminal α-galactosyl moiety.

  本发明涉及治疗学领域，更具体地说，涉及用于预防和/或治疗由胃肠道细菌引起的受试者感染的制剂和组合物，所述制剂和组合物基于包含末端α-半乳糖基分子的制剂。