N-chloroacetyl-β-D-galactopyranosylamine | 183583-59-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-chloroacetyl-β-D-galactopyranosylamine
• 英文别名: N-(β-D-galactopyranosyl)chloroacetamide；β-D-Galp-NHCOCH2Cl；N-chloroacetyl-beta-d-galactopyranosylamine；2-chloro-N-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]acetamide
• CAS: 183583-59-7
• 化学式: C₈H₁₄ClNO₆
• 分子量: 255.655
• InChiKey: KYUJZNBOUYNSAF-YTLSDQODSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  119
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-chloroacetyl-β-D-galactopyranosylamine 在 ammonium hydroxide 作用下， 反应 40.0h， 以70%的产率得到N-glycyl-β-D-galactopyranosylamine
  参考文献：
  名称：

  N-glycyl-β-glycopyranosylamines，单糖和二糖的衍生物，以及它们在制备羧酸糖缀合物中的用途

  摘要：

  为合成 N-甘氨酰-β-吡喃葡萄糖胺、单糖衍生物（d-半乳糖、d-甘露糖、l-岩藻糖和 N-乙酰-d-葡糖胺）和二糖（乳糖、蜜二糖、纤维二糖、和麦芽糖）。这些化合物被证明可用于制备含有羧基的生物活性化合物（烟碱酸、乳清酸、犬尿酸和吲哚乙酸）的糖缀合物。开发了使用丙二酸和l-酒石酸衍生物将N-甘氨酰-β-吡喃葡萄糖胺转化为含有羧基的衍生物的合成途径。

  DOI：

  10.1007/bf02495096
• 作为产物：
  描述：

  1-氨基-1-脱氧-beta-D-半乳糖 、 氯乙酸酐 以 甲醇 为溶剂， 以60%的产率得到N-chloroacetyl-β-D-galactopyranosylamine
  参考文献：
  名称：

  Crystal Structures of β‐1‐N‐Chloroacetamido Derivatives of d‐Glucose and d‐Galactose

  摘要：

  Crystal structures of 1-N-(beta-D-glucopyranosyl)chloroacetamide (1), an inhibitor of glycogen phosphorylase, and the corresponding galactopyranosyl amide (2) have been determined. Both crystals belong to P2(1)2(1)2(1) space group with 1 having the unit cell dimensions of a=7.939(3), b=9.547(3) and c=14.157(2) Angstrom, while those of 2 are, a=7.636(10), b=9.004(8) and c=14.807(5) Angstrom. The sugar ring takes a C-4(1) conformation and the amide linkage exists in Z-anti conformation in both crystals. The torsion angle O5-C1-N1-C1' is -93.9(5) for 1 and -111.5(3)degrees for 2. The conformational preference of C1 and N1 in 1 and 2 is found to be between anti and gauche. The molecular assembly in both 1 and 2 is stabilized by a finite chain of hydrogen bonds starting from N1H and ending at O1', whereas a ten membered hydrogen-bonded ring involving O4H and O5 is observed in 1.

  DOI：

  10.1081/car-120026600

文献信息

• Glycoconjugates of amino acids. Preparation throughN-alkylation of amino acids withN-chloroacetyl-β-glycopyranosylamines
  作者：L. M. Likhosherstov、O. S. Novikova、V. N. Shibaev

  DOI：10.1007/bf02495306

  日期：1999.7

  Monoalkylation of amino acids of different structural types withN-chloroacetyl-glycosylamines was shown to be applicable for the preparation of glycoconjugates containing β-d-galactose,N-acetyl-β-d-glucosamine, β-d-mannose, and lactose residues. The glycoconjugates were synthesized from amino acids with secondary (sarcosine,l-proline) or primary (l-2- and 4-aminobutyric acids,l-tryptophan) amino groups

  不同结构类型的氨基酸与 N-氯乙酰-糖胺的单烷基化被证明适用于制备含有 β-d-半乳糖、N-乙酰-β-d-葡糖胺、β-d-甘露糖和乳糖残基的糖缀合物。糖缀合物由具有二级（肌氨酸，l-脯氨酸）或一级（l-2-和4-氨基丁酸，l-色氨酸）氨基的氨基酸以及各种氨基二羧酸（N-甲基-dl-天冬氨酸、dl-天冬氨酸、l-谷氨酸和dl-2-氨基己二酸）。获得的衍生物可能对本系列生理活性化合物的糖靶向作用感兴趣。
• Enzymatic properties of α-d-galactosidase from Trichoderma reesei
  作者：Andrew N. Savel'ev、Farid M. Ibatyllin、Elena V. Eneyskaya、Anatoly M. Kachurin、Kirill N. Neustroev

  DOI：10.1016/s0008-6215(96)00248-0

  日期：1996.12

  compounds have been obtained. The inhibiting properties of the competitive inhibitors of d -galactose, 1,5-anhydro- d -galactitol, and 2-deoxygalactose have been compared, and reasons for differences in KI values between these compounds have been discussed. It has been shown that α- d -galactosidase exhibits transglycosylating activity; the main product of transglycosylation in the reaction with PNPG is p-nitrophenyl

  摘要天然和合成底物[甲基纤维素，棉子糖，水苏糖，甲基α-d-吡喃半乳糖苷和对硝基苯基α-d-吡喃半乳糖苷（PNPG）]的水解动力学，由α-d-半乳糖苷酶催化。真菌里氏木霉，已被研究。已经合成了许多作为α-d-半乳糖苷酶的竞争性抑制剂的N-酰基-α-d-吡喃半乳糖苷胺，并且已经获得了这些化合物的KI值。比较了d-半乳糖，1,5-脱水d-半乳糖醇和2-脱氧半乳糖的竞争性抑制剂的抑制性能，并讨论了这些化合物之间KI值差异的原因。已经显示出α-d-半乳糖苷酶表现出转糖基化活性。与PNPG反应的转糖基化的主要产物是对硝基苯基6-O-α-d-吡喃半乳糖苷-α-d-吡喃半乳糖苷。已显示在底物存在下的水解抑制与底物转糖基化相关。稳态动力学的数据以及通过停流方法获得的稳态前的动力学数据表明，在反应中形成了中间半乳糖基-酶复合物，在所研究的过程中特别重要。提出了描述所获得的实验数据的最小动力学方案。稳态动力学
• Glycoconjugates of amines: alkylation of primary and secondary amines withN-chloroacetyl-β-glycopyranosylamines
  作者：L. M. Likhosherstov、O. S. Novikova、V. N. Shibaev

  DOI：10.1007/bf02503499

  日期：1998.6

  Efficient monoalkylation of a series of primary and secondary amines was demonstrated with the use ofN-chloroacetylglycosylamines derived fromd-glucose,d-galactose,d-mannose,N-acetyl-d-glucosamine, and lactose. The reaction was shown to be useful for incorporation of carbohydrate residues into physiologically active compounds. Glycoconjugates of some derivatives of piperazine, 2-phenylethylamine, tryptamine

  使用衍生自 d-葡萄糖、d-半乳糖、d-甘露糖、N-乙酰基-d-葡糖胺和乳糖的 N-氯乙酰基糖胺证明了一系列伯胺和仲胺的有效单烷基化。该反应被证明可用于将碳水化合物残基结合到生理活性化合物中。制备了哌嗪、2-苯乙胺、色胺和重要生物胺（去甲麻黄碱、章鱼胺、多巴胺）的一些衍生物的糖缀合物。
• Synthesis of β-d-galactopyranosylamine derivatives with the terminal amino group in the spacer as mono-, di-, and trivalent ligands of galectins
  作者：L. M. Likhosherstov、O. S. Novikova、G. V. Mokrov

  DOI：10.1007/s11172-008-0345-8

  日期：2008.11

  Glycoclusters were obtained by N-alkylation of N-glycyl-β-d-galactopyranosylamine with N-chloroacetyl derivatives of β-d-galactopyranosylamine and N,N″-iminodiacetyl-di-β-d-galactopyranosylamine. The glycoclusters with two and three galactopyranosylamine residues and the monovalent ligand N-diglycyl-β-d-galactopyranosylamine with an amino group in the spacer are suitable for subsequent conjugation with carboxyl-containing physiologically active compounds.

  通过 N-甘氨酰-β-d-吡喃半乳糖胺与β-d-吡喃半乳糖胺的 N-氯乙酰衍生物和 N,N″-亚氨基二乙酰基-二-β-d-吡喃半乳糖胺的 N-烷基化作用，获得了聚糖簇。具有两个和三个吡喃半乳糖胺残基的聚糖簇，以及在间隔中带有一个氨基的单价配体 N-二甘氨酰-β-d-吡喃半乳糖胺，都适用于随后与含羧基的生理活性化合物共轭。
• Synthesis ofN-chioroacetyl-?-glycopyranosylamines, derivatives of monosaccharides and lactose
  作者：L. M. Likhosherstov、O. S. Novikova、V. N. Shibaev、N. K. Kochetkov

  DOI：10.1007/bf01431821

  日期：1996.7

  N-Chloroacetyl-beta-glycosylamines were synthesized from various monosaccharides (hexoses, pentoses, deoxysugars, uronic acids, and sugar phosphates) and a disaccharide (lactose) by N-acylation of the corresponding beta-glycosylamines with chloroacetic anhydride in DMF. In some cases, treatment of monosaccharides with NH3 in the presence of (NH4)CO3 in MeOH or aqueous MeOH was more efficient than the methods previously described, as it gave beta-glycosylamines in higher yields.