CAS: 68733-26-6; (2R,3R,4R,5R)-2-Azido-3,4,5,6-Tetrahydroxyhexanal

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2-氨基-2-脱氧-D-半乳糖盐酸盐置于copper(Ll) Sulfate Pentahydrate,碳酸氢钠,Triflic Azide体系中,用 水,甲醇 作为反应溶剂,化学反应生成 2-叠氮基-2-脱氧-D-半乳糖
参考文献:豇豆花叶病毒衣壳:用于开发基于碳水化合物的抗肿瘤疫苗的有前途的载体.
标题:豇豆花叶病毒衣壳:用于开发基于碳水化合物的抗肿瘤疫苗的有前途的载体.
摘要:针对肿瘤细胞表面碳水化合物的免疫疗法是一种有前途的癌症治疗方法.然而,碳水化合物的低免疫原性提出了巨大的挑战.我们在这里描述了通过豇豆花叶病毒(cpmv)衣壳表面的有序展示来增强碳水化合物的免疫原性. Tn 聚糖在许多癌细胞表面过度表达,被选为我们研究的模型抗原.此前已有研究表明,针对不同载体上以多种方式呈现的单体形式的 Tn,很难诱导出强烈的 T 细胞依赖性免疫反应.在这项研究中,我们首先合成了由马来酰亚胺或溴乙酰胺部分衍生的 Tn 抗原,该部分选择性地与 Cpmv 的半胱氨酸突变体缀合.然后将糖缀合物注射到小鼠体内,并通过酶联免疫吸附测定法测量免疫前和免疫后小鼠血清中的抗体水平.在免疫后第 35 天的血清中获得了高总抗体滴度,更重要的是,高 Tn 特异性 Igg 滴度,表明糖缀合物诱导了 T 细胞依赖性抗体同种型转换.反应生成的抗体能够识别 Mcf-7 乳腺癌细胞和多药耐药乳腺癌细胞系 Nci-Adr
DOI:10.1002/chem.200800203

专利信息

专利号:US-4362720-A
优先权日:1977-04-14
标题:Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals
发明人：LEMIEUX RAYMOND U; RATCLIFFE R MURRAY
权利人:CHEMBIOMED LTD
摘要:O-acetylated glycals react with ceric ammonium nitrate in the presence of sodium azide to provide, in good yield, O-acetylated 2-azido-2-deoxy glycosyl nitrates. These nitrates can be used to prepare 2-amino-2-deoxy sugars, such as D-galactosamine and lactosamine. The O-acetylated 2-azido-2-deoxy glycosyl nitrates can alternately be converted to O-acetylated 2-azido-2-deoxy glycosyl halides which are useful in the preparation of O-acetylated 2-azido-2-deoxy glycosides, which in turn can be reduced to 2-amino-2-deoxy glycosides. Of particular interest are the syntheses of 2-amino-2-deoxy glycosides which correspond to the terminal units of the antigenic determinant for the human A blood group. Attachment of these glycosides to a solid support provides immunoabsorbents which efficiently and preferentially absorb anti-A antibodies from blood plasma.

专利号:US-4308376-A
优先权日:1977-04-14
标 题 :Synthesis of 2-amino-2-deoxyglycoses and 2-amino-2-deoxyglycosides from glycals
发明人：LEMIEUX RAYMOND U; RATCLIFFE R MURRAY
权利人:CHEMBIOMED LTD
摘要:O-acetylated glycals react with ceric ammonium nitrate in the presence of sodium azide to provide, in good yield, O-acetylated 2-azido-2-deoxy glycosyl nitrates. These nitrates can be used to prepare 2-amino-2-deoxy sugars, such as D-galactosamine and lactosamine. The O-acetylated 2-azido-2-deoxy glycosyl nitrates can alternately be converted to O-acetylated 2-azido-2-deoxy glycosyl halides which are useful in the preparation of O-acetylated 2-azido-2-deoxy glycosides, which in turn can be reduced to 2-amino-2-deoxy glycosides. Of particular interest are the syntheses of 2-amino-2-deoxy glycosides which correspond to the terminal units of the antigenic determinant for the human A blood group. Attachment of these glycosides to a solid support provides immunoabsorbents which efficiently and preferentially absorb anti-A antibodies from blood plasma.

专利号:US-5837830-A
优先权日:1994-03-09
标 题 :Stereodirected process for synthesis of α-N-acetylgalactosaminides
发明人：KOGANTY RAO R; GANDHI SHAM
权利人:BIOMIRA INC
摘要:A stereodirected process for synthesizing alpha -N-acetylgalactosaminides from N-acetylgalactosamine which, in a preferred embodiment, comprises: reacting N-acetylgalactosamine with a dialkyl acetal of an aldehyde or ketone to form a 4,6-O-alkylidene derivative; reacting said 4,6-O-alkylidene derivative with a protecting group compound to attach a protecting group selectively to 3-OH of said derivative to form a 3-O-protected derivative; reacting said 3-O-protected derivative with an anomeric group to form a glycosyl donor; reacting said glycosyl donor with an alcohol to form an N-acetylgalactosaminide.

专利号:AU-2020409711-A1
优先权日:2019-12-20
标题 :Synthesis of lactone derivatives and their use in the modification of proteins

专利号:EP-0788504-A1
优先权日:1994-03-09
标 题:Stereodirected process for synthesis of alpha-n-acetylgalactosaminides

专利号:DE-4009634-A1
优先权日:1990-03-26
标 题:LACTON FORMATION AS A NEW PRINCIPLE OF THE ANOMERIC ACTIVATION OF CARBOHYDRATES FOR THE SYNTHESIS OF GLYCOSIDES AND SACCHARIDES: 1-0-ALKINE CARBONIC ACID ESTERES OF CARBOHYDRATES