胞苷-5'-单磷酸-N-乙酰神经氨酸 | 55569-66-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 中文名称: 胞苷-5'-单磷酸-N-乙酰神经氨酸
• 英文名称: cytidine 5'-monophosphate-N-acetylneuraminic acid
• 英文别名: cytidine 5'-monophospho-N-acetylneuraminic acid；cytidine-5'-monophospho-N-acetylneuraminic acid；cytidine monophosphate N-acetylneuraminic acid；cytidine monophosphate-N-acetylneuramic acid；CMP-N-acetylneuraminic acid；β-Neu5AcCMP；(2S,4S,5R,6R)-5-Acetamido-2-[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• CAS: 55569-66-9
• 化学式: C₂₀H₃₁N₄O₁₆P
• 分子量: 614.457
• InChiKey: TXCIAUNLDRJGJZ-RKSFOSEPSA-N

物化性质

• 密度：
  2.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.7
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  321
• 氢给体数：
  10
• 氢受体数：
  16

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  5'-胞苷酸	cytidine monophosphate	63-37-6	C9H14N3O8P	323.199
  ——	4-nitrophenyl O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->6)-β-D-galactopyranoside	81119-31-5	C23H32N2O16	592.511
  N-乙酰神经氨酸水合物	sialic acid	21646-00-4	C11H19NO9	309.273

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-5-(1,3-dioxoisoindol-2-yl)-4-hydroxy-2-(hydroxymethyl)-6-phenylsulfanyloxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid	751477-16-4	C37H46N2O19S	854.84
  ——	Ac-Tyr-Asp-Phe-Leu-Pro-Glu-Thr(NeuAc(α2,3)Galβ(1,4)GlcNAc(β1,6)GalNAcα)-Glu-NH2	262283-36-3	C82H120N12O40	1913.91
  ——	phenyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonate)-(2-3)-O-(β-D-galactopyranosyl)-(1-4)-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside	744193-99-5	C32H45Cl3N2O19S	900.136
  ——	dodecyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonic acid)-(2->8)-5-acetamido-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-non-2-ulopyranosidonic acid	1186201-35-3	C34H60N2O16S	784.92
  ——	4-nitrophenyl O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->6)-β-D-galactopyranoside	81119-31-5	C23H32N2O16	592.511
  ——	4-nitrophenyl O-(5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosylonic acid)-(2->3)-β-D-galactopyranoside	81123-28-6	C23H32N2O16	592.511
  ——	ethyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)(2<*>3)-O-(β-D-galactopyranosyl)(1<*>4)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)(1<*>3)-β-D-galactopyranoside	164112-47-4	C33H56N2O24	864.807
  ——	8-(methoxycarbonyl)octyl O-(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2<*>3)-O-β-D-galactopyranosyl-(1<*>4)-2-acetamido-2-deoxy-β-D-glucopyranoside	122290-73-7	C35H60N2O21	844.862
  ——	2-acetamido-6-O-(5-acetamido-3,5-didesoxy-D-glycero-α-D-galacto-2-nonulopyranosylonsaeure)-2-desoxy-D-galactopyranose	120906-42-5	C19H32N2O14	512.468
  ——	(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2→3)-β-D-galactopyranosyl-(1→4)-β-D-glucopyranosyl-(1→1)-(2S,3R,4E)-2-amino-4-octadecene-1,3-diol	94458-63-6	C41H74N2O20	915.04

反应信息

• 作为反应物：
  描述：

  胞苷-5'-单磷酸-N-乙酰神经氨酸 在 苯磺酰胺 、 fuc-t VI 、 sodium cacodylate buffer 、 magnesium chloride 作用下， 以 水 为溶剂， 反应 96.0h， 生成 8-methoxycarbonyloctyl 5-N-acetyl-α-neuraminyl-(2->3)-β-D-galactopyranosyl-(1->4)-[α-L-fucopyranosyl-(1->3)]-2-deoxy-2-(methyl-β-D-galactohexopyranosyluronamide)-β-D-glucopyranoside
  参考文献：
  名称：

  Glycosyl-transferase catalyzed assemblage of sialyl-lewis x -saccharopeptides

  摘要：

  A series of glycohexopyranuronic acids are coupled to glucosamines to give 'disaccharides' which have the natural N-acetyl group of the glcNAc-moiety replaced by various sugar acids (-->saccharopeptides). These saccharopeptides are surprisingly good substrates for beta(1-4)galactosyl-transferase, alpha(2-3)sialyl-transferase, and fucosyl-transferase VI. The enzymes transfer successively galactose, sialic acid, and fucose from the corresponding donors onto these acceptor substrates-despite the far reaching alterations-regio- and stereospecifically in the expected manner to yield a new class of compounds, the sialyl-Lewis(x)-saccharopeptides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00107-2
• 作为产物：
  描述：

  N-乙酰神经氨酸水合物 、 5'-胞苷酸 在 UMP/CMP kinase inorganic polyphosphate 、 三羟甲基氨基甲烷盐酸盐 、 magnesium chloride 作用下， 以 various solvent(s) 为溶剂， 生成 胞苷-5'-单磷酸-N-乙酰神经氨酸
  参考文献：
  名称：

  酶促合成CMP-NeuAc的新方法。

  摘要：

  建立了一种新型的CMP-NeuAc合成方法。我们首先证实，流感嗜血杆菌的推定的neuA基因（由其整个基因组序列计划确定）确实编码CMP-NeuAc合成酶（EC 2.7.7.43）。该酶需要CTP作为NeuAc的胞嘧啶化的胞嘧啶供体。将该酶与由CMP和无机多磷酸盐作为唯一的磷酸供体的酶促CTP生成系统耦合，该磷酸供体是由多磷酸盐激酶和CMP激酶的组合驱动的，其中CMP的磷酸化由两种酶表达的联合活性完成，随后多磷酸激酶本身可以使CDP磷酸化。将流感嗜血杆菌的CMP-NeuAc合成酶，多磷酸激酶和CMP激酶添加到含有等摩尔浓度（15 mM）的CMP和NeuAc的反应混合物中时，

  DOI：

  10.1271/bbb.65.1736

文献信息

• A Novel Linker Methodology for the Synthesis of Tailored Conjugate Vaccines Composed of Complex Carbohydrate Antigens and Specific T_H‐Cell Peptide Epitopes
  作者：Sebastian Dziadek、Sandra Jacques、David R. Bundle

  DOI：10.1002/chem.200800065

  日期：2008.6.27

  protein (hsp60). Moreover, the linkage chemistry has proven well suited for the synthesis of more complex target structures such as a biotinylated glycopeptide, a three component vaccine containing an immunostimulatory peptide epitope from interleukin-1 beta (IL-1 beta), and for the conjugation of complex carbohydrates to carrier proteins such as bovine serum albumin.

  致病生物或致癌转化细胞通常在其细胞表面表达复杂的碳水化合物结构，这是主动免疫疗法的可行目标。我们在这里描述了一种新型的，免疫中性的，用于高效制备结合复杂糖抗原与特定TH细胞肽表位的高清晰度疫苗偶联物的方法。这种新颖的异双功能方法被用于从致病性真菌白色念珠菌中将（1-> 2）-β-甘露聚糖三糖以及肿瘤相关神经节苷脂GM2的碳水化合物部分与TH细胞肽表位偶联鼠60 kDa自热休克蛋白（hsp60）。此外，事实证明，连接化学非常适合合成更复杂的目标结构，例如生物素化糖肽，
• Chemoenzymatic synthesis of PSGL-1 glycopeptides: sulfation on tyrosine affects glycosyltransferase-catalyzed synthesis of the O -glycan
  作者：Kathryn M Koeller、Mark E.B Smith、Chi-Huey Wong

  DOI：10.1016/s0968-0896(00)00041-9

  日期：2000.5

  PSGL-1 is the primary glycoprotein ligand for P-selectin during the inflammatory response. Interestingly, the N-terminal sequence, containing both a site of tyrosine sulfation and an O-glycan, has been shown to bind to P-selectin with an affinity similar to full-length PSGL-1. To further characterize this system, the synthesis of glycopeptides from PSGL-1 was undertaken. The synthesis involved both solution-

  PSGL-1是炎症反应过程中P-选择蛋白的主要糖蛋白配体。有趣的是，已显示同时包含酪氨酸硫酸化位点和O-聚糖的N末端序列以与全长PSGL-1相似的亲和力与P-选择素结合。为了进一步表征该系统，进行了从PSGL-1合成糖肽的研究。合成涉及溶液和固相合成，以及酶促转化。在合成期间，观察到糖基转移酶对相同糖肽的硫酸化和未硫酸化形式的显着反应性差异。
• Chemical and Chemoenzymatic Synthesis of S-Linked Ganglioside Analogues and Their Protein Conjugates for Use as Immunogens
  作者：Jamie R. Rich、Warren W. Wakarchuk、David R. Bundle

  DOI：10.1002/chem.200500518

  日期：2006.1.11

  Analogues of the tumor-associated gangliosides GM(3) and GM(2) containing terminal S-linked neuraminic acid residues and an amino terminated, truncated ceramide homologue have been synthesized and conjugated to a protein. The synthesis involved coupling of a S-linked sialyl alpha(2-->3) galactose disaccharide with a glucosyl sphingosine analogue, followed by elaboration and deprotection to give amino-terminated

  合成了与肿瘤相关的神经节苷脂GM（3）和GM（2）的类似物，这些神经节苷脂含有末端S连接的神经氨酸残基和一个氨基末端，截短的神经酰胺同系物，并与蛋白质偶联。合成过程包括将S-连接的唾液酸α（2-> 3）半乳糖二糖与葡萄糖基鞘氨醇类似物偶联，然后进行精制和脱保护，得到氨基末端的糖基神经酰胺1。糖基转移酶催化的三糖1的延伸提供了可及性。修饰的GM（2）四糖2或含硫的GD（3）类似物30。由于它们对内源性糖苷水解酶的潜在抗性增强以及其固有的非自身特性，含有非还原性末端硫糖苷键的糖类抗原可能比O型连接的抗原更具免疫原性，并且可以刺激能够识别天然存在的寡糖的抗体的产生。我们的初步结果表明，实际上这些抗原是可行的免疫原，此外，在异源糖蛋白结合物的情况下，免疫血清与O-神经节苷脂发生交叉反应。
• Specific crosslinking of cell adhesive molecules by heterobifunctional glycopeptide synthesised on the basis of chemoenzymatic strategy
  作者：Shin-Ichiro Nishimura、Masao Matsuda、Hidemitsu Kitamura、Takashi Nishimura

  DOI：10.1039/a904362d

  日期：——

  Heterobifunctional glycopeptide 1 composed of Neu5Acα-(2→3)Galβ(1→4)[Fucα(1→3)]GlcNAc (sialyl Lewisx) and Lys-Gly-Arg-Gly-Asp-Ser (KGRGDS) having specific activity to bind concurrently with two different types of cell adhesive molecules such as selectins and integrins was synthesised on the basis of a combined chemical and enzymatic strategy.

  异双功能糖肽1由Neu5Acα-(2→3)Galβ(1→4)[Fucα(1→3)]GlcNAc（唾液酸Lewisx）和Lys-Gly-Arg-Gly-Asp-Ser（KGRGDS）组成，具有同时与两种不同类型细胞粘附分子（如选择素和整合素）结合的特定活性，基于综合的化学与酶促策略合成。
• Heterobifunctional Ligands:  Practical Chemoenzymatic Synthesis of a Cell Adhesive Glycopeptide That Interacts with Both Selectins and Integrins
  作者：Masao Matsuda、Shin-Ichiro Nishimura、Fumio Nakajima、Takashi Nishimura

  DOI：10.1021/jm000295r

  日期：2001.3.1

  modulator of cellular recognition is described. A nonnatural glycopeptide 1 composed of sialyl Lewis x and Lys-Gly-Arg-Gly-Asp-Ser that interacts with both selectins and integrins has been systematically synthesized by combined chemical and enzymatic strategy. It is suggested that glycopeptide 1 showed much higher affinity with P-selectin (K(a) = 6.6 x 10(7) M(-1)) and E-selectin (K(a) = 4.5 x 10(5) M(-1))

  作为一种新型的细胞识别调节剂，描述了一种具有独特特性的细胞黏附糖肽的有效合成方法。已通过化学和酶联策略系统地合成了由唾液酸化的路易斯x和Lys-Gly-Arg-Gly-Asp-Ser组成的，与选择素和整联蛋白相互作用的非天然糖肽1。建议糖肽1与P-选择素（K（a）= 6.6 x 10（7）M（-1））和E-选择素（K（a）= 4.5 x 10（5）M（ -1））。该化合物还比四肽Arg-Gly-Asp-Ser更有效地抑制了人类整联蛋白beta（1）及其单克隆抗体之间的特异性相互作用。有趣的是 表面等离子体共振分析表明，这种异双功能糖肽具有同时与P-选择蛋白和整联蛋白β（1）形成稳定复合物的能力。还建议该活性可以作为细胞迁移模型用于抑制整联蛋白介导的活化的辅助T细胞对胶原包被的板的粘附。这些结果表明碳水化合物和多肽的不同生物学功能的化学酶杂交策略是设计有效的糖缀合物作为抗炎和抗癌转移试剂的新