N-(2-benzyloxyacetyl)-d-mannosamine

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2-benzyloxyacetyl)-d-mannosamine
• 英文别名: N-Benzyloxyacetylmannosamine；2-phenylmethoxy-N-[(3S,4R,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• 化学式: C₁₅H₂₁NO₇
• 分子量: 327.334
• InChiKey: ZTDKVQIYPZMDQC-STYVAPRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  129
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(2-benzyloxyacetyl)-d-mannosamine 生成 N-glycolylmannosamine
  参考文献：
  名称：

  AUGE, CLAUDINE;DAVID, SERGE;GAUTHERON, CHRISTINE;MALLERON, ANNIE;CAVAYE, +, NEW J. CHEM., 12,(1988) N 8-9, C. 733-744

  摘要：

  DOI：
• 作为产物：
  描述：

  苄氧乙酸 、 D-mannosamine hydrochloride 在 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以69%的产率得到N-(2-benzyloxyacetyl)-d-mannosamine
  参考文献：
  名称：

  胞苷5'-单磷酸-唾液酸合成酶的工程改造，以提高对功能性唾液酸的耐受性

  摘要：

  AbstractSialic acid‐containing glycoconjugates at the cell surface are of high importance in carbohydrate‐mediated recognition phenomena in physiological and pathological events, as well as in bacterial or viral infection. A key step in the enzymatic synthesis of natural sialoconjugates and functional synthetic analogues is the activation of sialic acids to cytidine 5′‐monophosphate (CMP)‐sialic acid intermediates catalyzed by CMP‐sialic acid synthetase (CSS). Based on our recently developed aligned protein model of substrate binding and a simple colorimetric screening assay, we have engineered the CSS from Neisseria meningitidis by structure‐guided site‐specific saturation mutagenesis at positions 192/193 to generate enzymes with broadened substrate scope. Top hits, including the F192S/F193Y variant, display an improvement of up to 70‐fold catalytic efficiency relative to wild‐type CSS for the conversion of sterically demanding N‐acyl modified sialic acid analogues, without compromising protein stability. Such significantly enhanced substrate capacity is a major step forward to realizing a generalized chemo‐enzymatic strategy for the efficient preparation of neo‐sialoconjugate libraries, demonstrated by the highly efficient, regio‐ and stereospecific synthesis of 2,6‐sialyllactose analogues by enzymatic coupling to the highly substrate tolerant α2,6‐sialyltransferase from Photobacterium leiognathi JT‐SHIZ‐145. Our results further document the unusual versatility of the N. meningitidis CSS and engineered variants for a common synthetic approach to sialoconjugates comprising a large diversity of natural and non‐natural sialic acid forms without the need for post‐synthetic enzymatic modification.magnified image

  DOI：

  10.1002/adsc.201300568

文献信息

• Effective one-pot multienzyme (OPME) synthesis of monotreme milk oligosaccharides and other sialosides containing 4-O-acetyl sialic acid
  作者：Hai Yu、Jie Zeng、Yanhong Li、Vireak Thon、Baojun Shi、Xi Chen

  DOI：10.1039/c6ob01706a

  日期：——

  A facile one-pot two-enzyme chemoenzymatic approach has been established for the gram (Neu4,5Ac2α3Lac, 1.33 g) and preparative scale (Neu4,5Ac2α3LNnT) synthesis of monotreme milk oligosaccharides. Other O-acetyl-5-N-acetylneuraminic acid (Neu4,5Ac2)- or 4-O-acetyl-5-N-glycolylneuraminic acid (Neu4Ac5Gc) -containing α2-3-sialosides have also been synthesized in the preparative scale. Used as an effective

  一种简便一锅双酶酶法方法已建立了克（Neu4,5Ac 2 α3Lac，1.33克）和制备规模（Neu4,5Ac 2单孔类动物乳寡糖α3LNnT）的合成。还已经以制备规模合成了其他的含O-乙酰基-5- N-乙酰基神经氨酸（Neu4,5Ac 2）或4 - O-乙酰基-5- N-羟基乙酰神经氨酸（Neu4Ac5Gc）的α2-3唾液酸。作为一种有效的探针，Neu4,5Ac 2 α3Galβ p NP被发现是通过人的A型流感病毒但不细菌唾液酸酶的合适底物。
• Efficient chemoenzymatic synthesis of sialyl Tn-antigens and derivatives
  作者：Li Ding、Hai Yu、Kam Lau、Yanhong Li、Saddam Muthana、Junru Wang、Xi Chen

  DOI：10.1039/c1cc12732b

  日期：——

  An N-terminal and C-terminal truncated recombinant α2–6-sialyltransferase cloned from Photobacterium sp. JH-ISH-224, Psp2,6ST(15–501)-His6, was shown to be an efficient catalyst for one-pot three-enzyme synthesis of sialyl Tn (STn) antigens and derivatives containing natural and non-natural sialic acid forms.

  从发光杆菌属克隆的 N 端和 C 端截短的重组 α2-6-唾液酸转移酶。 JH-ISH-224, Psp2,6ST(15–501)-His6，被证明是一锅三酶合成唾液酸 Tn (STn) 抗原和含有天然和非天然唾液酸形式的衍生物的有效催化剂。
• Chemoselective ligation
  申请人：——

  公开号：US20030199084A1

  公开（公告）日：2003-10-23

  The present invention features a chemoselective ligation reaction that can be carried out under physiological conditions. In general, the invention involves condensation of a specifically engineered phosphine, which can provide for formation of an amide bond between the two reactive partners resulting in a final product comprising a phosphine moiety, or which can be engineered to comprise a cleavable linker so that a substituent of the phosphine is transferred to the azide, releasing an oxidized phosphine byproduct and producing a native amide bond in the final product. The selectivity of the reaction and its compatibility with aqueous environments provides for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).

  本发明涉及一种可在生理条件下进行的化学选择性连接反应。一般而言，该发明涉及一种特别设计的膦化合物的缩合反应，该化合物可以提供两个反应物之间形成酰胺键，从而产生含有膦基团的最终产物，或者可以被设计成包含可断裂的连接基团，以便将膦基团的取代基转移给偶氮基，释放氧化膦副产物并在最终产物中产生天然酰胺键。该反应的选择性和其与水环境的兼容性使其适用于体内（例如，细胞表面或细胞内）和体外（例如，合成肽和其他聚合物，生产修饰的（例如，标记的）氨基酸）。
• CHEMOSELECTIVE LIGATION
  申请人：Saxon Eliana

  公开号：US20080214801A1

  公开（公告）日：2008-09-04

  The present invention features a chemoselective ligation reaction that can be carried out under physiological conditions. In general, the invention involves condensation of a specifically engineered phosphine, which can provide for formation of an amide bond between the two reactive partners resulting in a final product comprising a phosphine moiety, or which can be engineered to comprise a cleavable linker so that a substituent of the phosphine is transferred to the azide, releasing an oxidized phosphine byproduct and producing a native amide bond in the final product. The selectivity of the reaction and its compatibility with aqueous environments provides for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).

  本发明涉及一种可在生理条件下进行的化学选择性连接反应。一般而言，该发明涉及特别设计的膦化合物的缩合反应，该膦化合物可以提供在两个反应物之间形成酰胺键的反应，从而产生包含膦基团的最终产物，或者可以被设计成包含可切断的连接剂，以便将膦的取代基转移到偶氮化物上，释放氧化的膦副产物并在最终产物中产生天然的酰胺键。该反应的选择性及其与水环境的兼容性使其适用于体内应用（例如，在细胞表面或细胞内）和体外应用（例如，合成肽和其他聚合物，生产修饰（例如，标记）的氨基酸）。
• CHEMOSELECTIVE LIGATION
  申请人：Saxon Eliana

  公开号：US20110236930A1

  公开（公告）日：2011-09-29

  The present invention features a chemoselective ligation reaction that can be carried out under physiological conditions. In general, the invention involves condensation of a specifically engineered phosphine, which can provide for formation of an amide bond between the two reactive partners resulting in a final product comprising a phosphine moiety, or which can be engineered to comprise a cleavable linker so that a substituent of the phosphine is transferred to the azide, releasing an oxidized phosphine byproduct and producing a native amide bond in the final product. The selectivity of the reaction and its compatibility with aqueous environments provides for its application in vivo (e.g., on the cell surface or intracellularly) and in vitro (e.g., synthesis of peptides and other polymers, production of modified (e.g., labeled) amino acids).

  本发明涉及一种可以在生理条件下进行的化学选择性连接反应。一般来说，本发明涉及特别设计的膦化合物的缩合，该膦化合物可以提供在两个反应物之间形成酰胺键，从而产生包含膦基团的最终产物，或者可以被设计为包含可断裂的连接器，以便将膦的取代基转移到偶氮化物上，释放出氧化的膦副产物并在最终产物中产生天然的酰胺键。该反应的选择性及其与水相环境的兼容性使其适用于体内（例如，细胞表面或细胞内）和体外（例如，合成肽和其他聚合物，生产修饰的（例如，标记的）氨基酸）。