N-[(2S)-1-[6-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexylamino]-1-oxo-3-phenylpropan-2-yl]-6-(prop-2-enoylamino)hexanamide | 174272-05-0

• 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: N-[(2S)-1-[6-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexylamino]-1-oxo-3-phenylpropan-2-yl]-6-(prop-2-enoylamino)hexanamide
• CAS: 174272-05-0
• 化学式: C₃₂H₅₀N₄O₉
• 分子量: 634.77
• InChiKey: RILNJLJNQFIVQH-OVRIQYAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  45
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  尿苷 5’-二二氧磷基半乳糖二钠盐 、 cytidine-5'-monophosphono-N-acetylneuraminic acid 、 N-[(2S)-1-[6-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexylamino]-1-oxo-3-phenylpropan-2-yl]-6-(prop-2-enoylamino)hexanamide 在 盐酸 、 苯磺酰胺 、 sodium azide 、 四甲基乙二胺 、 α-2->6-sialyltransferase 、 galactosyl transferase 、 HEPES buffer 、 sodium cacodylate buffer 、 丙烯酰胺 、 6-氨基-9-[3,4-二羟基-5-[(羟基-磺基氧基-磷酰)氧基甲基]四氢呋喃-2-基]-嘌呤 、 manganese(ll) chloride 、 α-chymotrypsin 、 α-lactalbumin 作用下， 生成 (2R,4S,5R,6R)-5-acetamido-2-[[(2R,3R,4S,5R,6S)-6-[(2R,3S,4R,5R,6R)-5-acetamido-6-(6-aminohexoxy)-4-hydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
  参考文献：
  名称：

  High performance polymer supports for enzyme-assisted synthesis of glycoconjugates

  摘要：

  Efficient and practical methodology for the construction of carbohydrates, including oligosaccharide derivatives and sphingoglycolipids, was established on the basis of a water-soluble polymer supports having unique linkers that can be cleaved by specific conditions. Novel glycomonomers for the construction of polymer supports were synthesized and copolymerized with acrylamide to give three types of water-soluble glycopolymers having primer sugars through the specific linkers containing (i) p-substituted benzyl group, (ii) L-phenylalanine residue, and (iii) ceramide-mimetic L-serine derivative, respectively. These glycopolymers were employed for sugar elongation reactions with glycosyl transferases such as GlcNAc beta 1,4-galactosyl transferase, beta Gal1-->3/4GlcNAc alpha-2,6-sialyl transferase, and beta Gal1-->3/4GlcNAc alpha-2,3-sialyl transferase in the presence of each sugar nucleotide as glycosyl donor to afford polymers having N-acetyllactosamine, sialyl alpha-(2-->6) N-acetyllactosamine, and sialyl alpha-(2-->3) lactose residues in excellent yield. Subsequent hydrogenolysis, hydrolysis with alpha-chymotrypsin, or transglycosylation to ceramide with ceramide glycanase proceeds smoothly to give N-acetyllactosamine, a versatile sialyl alpha-(2-->6) N-acetyllactosamine derivative having a terminal amino group, and ganglioside GM3 in high yield. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)10051-9
• 作为产物：
  描述：

  6-氨基-1-己醇 在 palladium on activated charcoal camphor-10-sulfonic acid 、 氢气 、 sodium methylate 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 甲醇 、 乙醇 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 87.5h， 生成 N-[(2S)-1-[6-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexylamino]-1-oxo-3-phenylpropan-2-yl]-6-(prop-2-enoylamino)hexanamide
  参考文献：
  名称：

  High performance polymer supports for enzyme-assisted synthesis of glycoconjugates

  摘要：

  Efficient and practical methodology for the construction of carbohydrates, including oligosaccharide derivatives and sphingoglycolipids, was established on the basis of a water-soluble polymer supports having unique linkers that can be cleaved by specific conditions. Novel glycomonomers for the construction of polymer supports were synthesized and copolymerized with acrylamide to give three types of water-soluble glycopolymers having primer sugars through the specific linkers containing (i) p-substituted benzyl group, (ii) L-phenylalanine residue, and (iii) ceramide-mimetic L-serine derivative, respectively. These glycopolymers were employed for sugar elongation reactions with glycosyl transferases such as GlcNAc beta 1,4-galactosyl transferase, beta Gal1-->3/4GlcNAc alpha-2,6-sialyl transferase, and beta Gal1-->3/4GlcNAc alpha-2,3-sialyl transferase in the presence of each sugar nucleotide as glycosyl donor to afford polymers having N-acetyllactosamine, sialyl alpha-(2-->6) N-acetyllactosamine, and sialyl alpha-(2-->3) lactose residues in excellent yield. Subsequent hydrogenolysis, hydrolysis with alpha-chymotrypsin, or transglycosylation to ceramide with ceramide glycanase proceeds smoothly to give N-acetyllactosamine, a versatile sialyl alpha-(2-->6) N-acetyllactosamine derivative having a terminal amino group, and ganglioside GM3 in high yield. (C) 1998 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(97)10051-9

文献信息

• An efficient synthesis of sialoglycoconjugates on a peptidase-sensitive polymer support
  作者：Kuriko Yamada、Shin-Ichiro Nishimura

  DOI：10.1016/0040-4039(95)02056-x

  日期：1995.12

  A novel method for the enzymatic synthesis of oligosaccharide derivatives on a alpha-chymotrypsin-sensitive polymer support is described. The primer polymer having N-acetyl-D-glucosamine (GlcNAc) residue through a phenylalanine-containing spacer moiety was successfully elongated with galactosyl and sialyltransferases to give a glycopolymer bearing sialyl alpha(2 --> 6) N-acetyllactosamine branches in high yield. Subsequent hydrolysis with alpha-chymotrypsin proceeded smoothly and afforded a versatile sialotrisaccharide derivative having a terminal amino group which can he used for creating neoglycoconjugates.
• High performance polymer supports for enzyme-assisted synthesis of glycoconjugates
  作者：Kuriko Yamada、Eriko Fujita、Shin-Ichiro Nishimura

  DOI：10.1016/s0008-6215(97)10051-9

  日期：1997.12

  Efficient and practical methodology for the construction of carbohydrates, including oligosaccharide derivatives and sphingoglycolipids, was established on the basis of a water-soluble polymer supports having unique linkers that can be cleaved by specific conditions. Novel glycomonomers for the construction of polymer supports were synthesized and copolymerized with acrylamide to give three types of water-soluble glycopolymers having primer sugars through the specific linkers containing (i) p-substituted benzyl group, (ii) L-phenylalanine residue, and (iii) ceramide-mimetic L-serine derivative, respectively. These glycopolymers were employed for sugar elongation reactions with glycosyl transferases such as GlcNAc beta 1,4-galactosyl transferase, beta Gal1-->3/4GlcNAc alpha-2,6-sialyl transferase, and beta Gal1-->3/4GlcNAc alpha-2,3-sialyl transferase in the presence of each sugar nucleotide as glycosyl donor to afford polymers having N-acetyllactosamine, sialyl alpha-(2-->6) N-acetyllactosamine, and sialyl alpha-(2-->3) lactose residues in excellent yield. Subsequent hydrogenolysis, hydrolysis with alpha-chymotrypsin, or transglycosylation to ceramide with ceramide glycanase proceeds smoothly to give N-acetyllactosamine, a versatile sialyl alpha-(2-->6) N-acetyllactosamine derivative having a terminal amino group, and ganglioside GM3 in high yield. (C) 1998 Elsevier Science Ltd.