2-(acetylamino)-2-deoxy-α-D-galactopyranosyl-L-threonine | 17041-35-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(acetylamino)-2-deoxy-α-D-galactopyranosyl-L-threonine
• 英文别名: O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine；2-acetamido-2-deoxy-α-D-galactopyranosyl-L-threonine；GalNAcα1-O-Thr；3-O-(2-Acetamido-2-desoxy-α-D-galactopyranosyl)-L-threonin；O-(N-acetyl-alpha-D-galactosaminyl)-L-threonine；(2S,3R)-3-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-aminobutanoic acid
• CAS: 17041-35-9；72274-72-7；116949-19-0；67315-18-8
• 化学式: C₁₂H₂₂N₂O₈
• 分子量: 322.315
• InChiKey: KUIFHYPNNRVEKZ-VIJRYAKMSA-N

物化性质

• 沸点：
  686.9±55.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  172
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(acetylamino)-2-deoxy-α-D-galactopyranosyl-L-threonine 、 4-硝基苯基-D-吡喃葡糖苷 在 β-galactosidase from bovine testes 、 sodium phosphate-citrate buffer 作用下， 以 水 为溶剂， 反应 48.0h， 以28%的产率得到3-{[3-乙酰氨基-5-羟基-6-(羟基甲基)-4-{[3,4,5-三羟基-6-(羟基甲基)四氢-2H-吡喃-2-基]氧基}四氢-2H-吡喃-2-基]氧基}-2-氨基丁酸
  参考文献：
  名称：

  Chemoenzymatic synthesis of the Thomsen-Friedenreich antigen determinant

  摘要：

  The efficient chemoenzymatic synthesis of the Thomsen-Friedenreich antigen determinant is demonstrated under transglycosylation conditions employing beta-galactosidase from bovine testes. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00324-2
• 作为产物：
  描述：

  3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride 在 palladium on activated charcoal calcium sulfate 、 sodium tetrahydroborate 、 silver carbonate 、 molecular sieve 、 氢气 、 硼酸 、 silver perchlorate 、 苯甲醇钠 、 nickel dichloride 、 苯甲醇 作用下， 以 吡啶 、 甲醇 、 乙醇 、 二氯甲烷 、 溶剂黄146 、 甲苯 为溶剂， 反应 507.0h， 生成 2-(acetylamino)-2-deoxy-α-D-galactopyranosyl-L-threonine
  参考文献：
  名称：

  合成糖肽O-β-d-吡喃半乳糖苷-（1→3）-O-（2-乙酰氨基-2-脱氧-α-d-吡喃半乳糖醛糖基）-（1→3）-l-丝氨酸和-l-苏氨酸

  摘要：

  摘要在碳酸银-高氯酸银和二氯甲烷-甲苯为溶剂的条件下，存在3,4,6-三-O-乙酰基-2-叠氮基-2-脱氧-β-d-吡喃半乳糖苷氯和1-丝氨酸衍生物和-1-苏氨酸，以高的立体选择性得到N-（苄氧羰基）-3-O-（3,4,6-三-O-乙酰基-2-叠氮基-2-脱氧-α-d的苄基酯对其进行氢解和解封，得到3-O-（2-乙酰氨基-脱氧-α-d-galactopyranosyl）-l-丝氨酸和-l，将-galactopyranosyl）-l-丝氨酸（7）和-l-苏氨酸（22）。 -苏氨酸分别对应于Tn抗原的半抗原。还原7的叠氮基，随后选择性的O-去乙酰化和苄基化，得到衍生物，其被2,3,4,6-四-O-乙酰基-α-d-吡喃半乳糖基溴化物糖基化以产生二糖。类似的反应顺序 从22开始，给出了1-苏氨酸类似物。从两种化合物中除去保护基，得到O-β-d-吡喃半乳糖基-（1→3）-O-（2-乙酰氨基-2-脱氧

  DOI：

  10.1016/0008-6215(82)84033-0

文献信息

• Chemoenzymatic Synthesis of Sialyl Oligosaccharides with Sialidases Employing Transglycosylation Methodology
  作者：Dirk Schmidt、Bernd Sauerbrei、Joachim Thiem

  DOI：10.1021/jo000871r

  日期：2000.12.1

  disease virus show a distinct preference for alpha(2-3) directed sialylations. Using combined chemical and enzymatic methodologies structures such as T-(Thomsen-Friedenreich) antigen [beta-D-Gal-(1-3)-alpha-D-GalNAc-OThr], Tn-(Thomsen nouveau) antigen (alpha-D-GalNAc-OThr) and beta-D-Gal-(1-4)-alpha-D-2-deoxy-Gal-OMe were sialylated in alpha(2-3)- and alpha(2-6)-positions regioselectively or in high

  利用霍乱弧菌，产气荚膜梭菌，鼠伤寒沙门氏菌和新城疫病毒的唾液酸酶的转糖活性，合成了一系列唾液寡糖。根据它们的水解活性，霍乱弧菌和产气荚膜梭菌的唾液酸酶优先催化唾液酸α（2-6）-键的形成，而伤寒沙门氏菌和新城疫病毒的唾液酸酶对α（2-3）表现出明显的偏爱。 ）定向唾液酸化。使用诸如T-（Thomsen-Friedenreich）抗原[β-D-Gal-（1-3）-α-D-GalNAc-OThr]的化学和酶学组合方法，在α（2-3）-中将Tn-（Thomsen nouveau）抗原（α-D-GalNAc-OThr）和β-D-Gal-（1-4）-α-D-2-脱氧-Gal-OMe唾液酸化。和α（2-6）-位置选择性或高区域异构体过量，并通过简单的分离程序纯化。取决于酶源和受体结构，转唾液酸化的产率在10％至30％之间变化。
• α-Selective glycosylation affords mucin-related GalNAc amino acids and diketopiperazines active on Trypanosoma cruzi
  作者：Maristela B. Martins-Teixeira、Vanessa L. Campo、Monica Biondo、Renata Sesti-Costa、Zumira A. Carneiro、João S. Silva、Ivone Carvalho

  DOI：10.1016/j.bmc.2013.01.027

  日期：2013.4

  This work addresses the synthesis and biological evaluation of glycosyl diketopiperazines (DKPs) cyclo[Asp-(alpha GalNAc)Ser] 3 and cyclo[Asp-(alpha GalNAc)Thr] 4 for the development of novel anti-trypanosomal agents and Trypanosoma cruzi trans-sialidase (TcTS) inhibitors. The target compounds were synthetized by coupling reactions between glycosyl amino acids alpha GalNAc-Ser 7 or alpha GalNAc-Thr 8 and the amino acid (O-tBu)-Asp 17, followed by one-pot deprotection-cyclisation reaction in the presence of 20% piperidine in DMF. The protected glycosyl amino acid intermediates 7 and 8 were, in turn, obtained by a-selective, HgBr2-catalysed glycosylation reactions of Fmoc-Ser/Thr benzyl esters 12/14 with alpha GalN(3)Cl 11, being, subsequently, fully deprotected for comparative biological assays. The DKPs 3 and 4 showed relevant anti-trypanosomal effects (IC50 282-124 mu M), whereas glycosyl amino acids 1 and 2 showed better TcTS inhibition (57-79%) than the corresponding DKPs (13-25%). (C) 2013 Elsevier Ltd. All rights reserved.
• Multienzyme System for Synthesis of the Sialylated Thomsen–Friedenreich Antigen Determinant
  作者：Ulrike Gambert、Joachim Thiem

  DOI：10.1002/(sici)1099-0690(199901)1999:1<107::aid-ejoc107>3.0.co;2-m

  日期：1999.1
• Scalable Synthesis of Fmoc-Protected GalNAc-Threonine Amino Acid and T_N Antigen via Nickel Catalysis
  作者：Fei Yu、Matthew S. McConnell、Hien M. Nguyen

  DOI：10.1021/acs.orglett.5b00780

  日期：2015.4.17

  The highly a-selective and scalable synthesis of the Fmoc-protected GalNAc-threonine amino acid and T-N antigen in gram scale (0.51 g) is described. The challenging 1,2-cis-2-amino glycosidic bond is addressed through a coupling of threonine residues with C(2)-N-ortho-(trifluoromethyl)benzylidenamino trihaloacetimidate donors mediated by Ni(4-F-PhCN)4(OTf)(2). The desired 1,2-cis-2-amino glycoside was obtained in 66% yield (3.77 g) with a-only selectivity and subsequently transformed into the Fmoc-protected GalNAc-threonine and T-N antigen. This operationally simple procedure no longer requires utilization of the commonly used C(2)-azido donors and overcomes many of the limitations associated with the synthesis of 1,2-cis linkage.
• Stereoselective Synthesis of Natural and Non-natural Thomsen-nouveau Antigens and Hydrazide Derivatives
  作者：Ahmad Ali Shaik、Sharmeen Nishat、Peter R. Andreana

  DOI：10.1021/acs.orglett.5b00512

  日期：2015.6.5

  A selective glycosylation strategy enabling access to all stereochemical combinations of tumor associated Thomsen-nouveau (Tn) antigen, d-GalNAc-O-Ser/Thr, has been developed. The key component for selectivity is the phthalimide-protected d- or l-amino acid acceptors which allow access to alpha- or beta-anomers in excellent yields (72-96%) and selectivity (similar to 100%) when appropriate C-2 substitution is installed. The glycoamino acid intermediates were divergently converted to Tn-based carboxylates or to hydrazides by tandem Pd-C debenzylation followed by treatment with hydrazine hydrate or hydrazine hydrate treatment alone.