6-(N-benzyloxycarbonyl L-phenylalanyl)-amino-1-hexanol | 174272-11-8

• 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: 6-(N-benzyloxycarbonyl L-phenylalanyl)-amino-1-hexanol
• 英文别名: benzyl N-[(2S)-1-(6-hydroxyhexylamino)-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 174272-11-8
• 化学式: C₂₃H₃₀N₂O₄
• 分子量: 398.502
• InChiKey: FHJQQMQLVUXVMU-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(N-benzyloxycarbonyl L-phenylalanyl)-amino-1-hexanol 在 palladium on activated charcoal camphor-10-sulfonic acid 、 氢气 、 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 48.5h， 生成 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-{6-[(S)-2-(6-acryloylamino-hexanoylamino)-3-phenyl-propionylamino]-hexyloxy}-tetrahydro-pyran-4-yl ester
  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 、 N-苄氧羰基-L-苯丙氨酸 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以85%的产率得到6-(N-benzyloxycarbonyl L-phenylalanyl)-amino-1-hexanol
  参考文献：
  名称：

  An efficient synthesis of sialoglycoconjugates on a peptidase-sensitive polymer support

  摘要：

  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.

  DOI：

  10.1016/0040-4039(95)02056-x

文献信息

• Sugar chain-containing water-soluble polymer compound
  申请人：Nishiguchi Susumu

  公开号：US20060287457A1

  公开（公告）日：2006-12-21

  A polymer compound having a monosaccharide or an oligosaccharide residue, or an amino acid or peptide residue bound to a monosaccharide or an oligosaccharide residue bound to a side chain of a water-soluble polymer through a linker containing a selectively cleavable bond, the water-soluble polymer containing 20 to 80 mol % of (meth)acrylic acid residue.

  这是一种聚合物化合物，它含有单糖或寡糖残基，或者氨基酸或肽残基与单糖或寡糖残基通过一个含有可选择断裂键的连接剂结合到水溶性聚合物的侧链上，其中水溶性聚合物含有20-80摩尔％的（甲基）丙烯酸残基。
• Method for producing glycoconjugates
  申请人：Toyo Boseki Kabushiki Kaisha

  公开号：EP0897014A2

  公开（公告）日：1999-02-17

  A method for producing glycoconjugate, which comprises the steps of: (i) binding a sugar residue to the side chain of a water-soluble polymer via a linker having a selectively cleavable linkage to give a primer, and bringing said primer into contact with an immobilized glycosyltransferase in the presence of a sugar nucleotide, to transfer a sugar residue of said sugar nucleotide to the sugar residue of said primer, (ii) elongating a sugar chain by transfer of plural sugar residues by repeating the step (i) at least once, (iii) removing, where necessary, a by-produced nucleotide or an unreacted sugar nucleotide, and (iv) repeating the steps (i)-(iii) where necessary and releasing the glycoconjugate by selectively cleaving the cleavable linkage in the linker, from the above-mentioned primer connecting the sugar chain elongated by the transfer of plural sugar residues, and a method for producing a sphingoglycolipid.

  一种生产糖共轭物的方法，包括以下步骤 (i) 通过具有选择性可裂解连接的连接体，将糖残基与水溶性聚合物的侧链结合，得到引物，并在糖核苷酸存在的情况下，使所述引物与固定的糖基转移酶接触，将所述糖核苷酸的糖残基转移到所述引物的糖残基上、 (ii) 重复步骤(i)至少一次，通过转移多个糖残基拉长糖链、 (iii) 必要时去除副产核苷酸或未反应的糖核苷酸，以及 (iv) 必要时重复步骤(i)-(iii)，通过选择性地裂解连接体中的可裂解连接，从上述连接通过转移多个糖残基拉长的糖链的引物中释放出糖共轭物、 以及一种生产鞘氨醇糖脂的方法。
• US6046040A
  申请人：——

  公开号：US6046040A

  公开（公告）日：2000-04-04
• US7700701B2
  申请人：——

  公开号：US7700701B2

  公开（公告）日：2010-04-20