1-戊胺,N-(3-甲基丁基)-N-亚硝基- | 73448-32-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 1-戊胺,N-(3-甲基丁基)-N-亚硝基-
• 英文名称: 4-methylumbelliferyl β-D-galactopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranoside
• 英文别名: Galβ1-4GlcNAcβMU；LacNAcβMU；4-methylumbelliferyl(4-MU)LacNAc；4MU-LacNAc；N-[(2S,3R,4R,5S,6R)-4-hydroxy-6-(hydroxymethyl)-2-(4-methyl-2-oxochromen-7-yl)oxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 73448-32-5；956-75-2
• 化学式: C₂₄H₃₁NO₁₃
• 分子量: 541.509
• InChiKey: AVXSAZHHBBNZIS-CYABAIRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.9
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  214
• 氢给体数：
  7
• 氢受体数：
  13

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  1-戊胺,N-(3-甲基丁基)-N-亚硝基- 在 Streptococcus pneumoniae β-galactosidase 、 Streptomyces plicatus β-N-acetylhexosaminidase 、 水 作用下， 生成 羟甲香豆素
  参考文献：
  名称：

  高通量糖基转移酶抑制法用于鉴定靶向癌细胞表面修饰中岩藻糖基化的分子。

  摘要：

  在癌症中，由于特定岩藻糖基转移酶（FUT）表达异常上调而导致的细胞表面聚糖上岩藻糖基化（岩藻糖残基的附着）增加，是与恶性肿瘤相关的最重要的聚糖修饰类型之一。在正常的生物过程以及疾病中，细胞表面的岩藻糖基化聚糖参与多种细胞相互作用和信号调节。例如，唾液酸化的LewisX是一种岩藻糖基化的细胞表面聚糖，在某些癌症中异常丰富，这与促进转移有关，它可使循环中的肿瘤细胞与血管内的上皮组织结合并通过利用聚糖介导的相互作用。为了鉴定FUT酶抑制剂作为潜在的癌症治疗剂，我们开发了一种新颖的高通量检测方法，该方法利用了荧光标记的寡糖作为岩藻糖基化的探针。该探针由4-甲基伞形糖基糖苷组成，可被特定的糖苷水解酶识别并水解，释放出荧光的4-甲基伞形酮，但当在用糖苷水解酶处理之前将岩藻糖基化时，不会发生水解，也不会发出荧光信号被生产。我们已经证明该测定法可用于测量小分子对FUT酶的抑制作用，因为阻断岩藻糖基化将使糖

  DOI：

  10.1021/acschembio.8b01123
• 作为产物：
  描述：

  glucose 1-phosphate 、 4-甲基香豆素-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷 在 E_. coli K-12 Glc-1-P uridylyltransferase 、 E_. coli UDP-galactose-4-epimerase 、 Neisseria meningitidis β1-4-galactosyltransferase encoded by lgtB gene 、 Pasteurella multocida inorganic pyrophosphatase 、 uridine 5’-(hydrogen triphosphate) 、 magnesium chloride 作用下， 以68%的产率得到1-戊胺,N-(3-甲基丁基)-N-亚硝基-
  参考文献：
  名称：

  Highly efficient chemoenzymatic synthesis of β1–4-linked galactosides with promiscuous bacterial β1–4-galactosyltransferases

  摘要：

  两种细菌β1→4-半乳糖基转移酶，NmLgtB 和 Hp1→4GalT，表现出杂乱且互补的受体底物特异性。它们已被用于高效的一锅多酶系统中，以单糖衍生物和廉价的Glc-1-P为原料合成 LacNAc、乳糖及其衍生物，包括含有带负电的6-O-磺酸化GlcNAc和C2取代的GlcNAc或Glc的衍生物。

  DOI：

  10.1039/c0cc01381a

文献信息

• SUGAR CHAIN CONTAINING 4-POSITION HALOGENATED GALACTOSE AND APPLICATION THEREOF
  申请人：Nishimura Shin-Ichiro

  公开号：US20090018327A1

  公开（公告）日：2009-01-15

  The present invention is directed to, for example, an oligosaccharide having at an end thereof a 4-position halogenated galactose residue represented by formula (I): (wherein X represents a halogen atom, and R represents a monosaccharide, an oligosaccharide, or a carrier), a transferase inhibitor containing the oligosaccharide, and a method for inhibiting sugar chain elongation reaction in the presence of glycosyltransferase, the method including employing the inhibitor. The invention also provides a method for producing a 4-position halogenated galactose sugar nucleotide represented by formula (II): (wherein each of R 1 to R 3 represents a hydroxyl group, an acetyl group, a halogen atom, or a hydrogen atom; X represents a halogen atom; and M represents a hydrogen ion or a metal ion), wherein the method employs bacterium-derived galactokinase and bacterium-derived hexose-1-phosphate uridylyltransferase. The invention is also directed to a sugar chain containing 4-position halogenated galactose envisaged to be employed as drugs and other materials, and to applications of the compound.

  本发明涉及一种寡糖，其末端具有由公式(I)表示的4位卤代半乳糖残基：（其中X代表卤素原子，R代表单糖，寡糖或载体），含有该寡糖的转移酶抑制剂，以及在存在糖基转移酶时抑制糖链延长反应的方法，该方法包括使用该抑制剂。该发明还提供了一种生产由公式(II)表示的4位卤代半乳糖核苷酸的方法：（其中R1至R3中的每一个代表羟基、乙酰基、卤素原子或氢原子；X代表卤素原子；M代表氢离子或金属离子），该方法利用细菌来源的半乳糖激酶和细菌来源的己糖-1-磷酸尿苷转移酶。本发明还涉及一种含有4位卤代半乳糖的糖链，可用作药物和其他材料，并涉及该化合物的应用。
• Cloning and characterization of a viral α2–3-sialyltransferase (vST3Gal-I) for the synthesis of sialyl Lewisx
  作者：Go Sugiarto、Kam Lau、Hai Yu、Stephanie Vuong、Vireak Thon、Yanhong Li、Shengshu Huang、Xi Chen

  DOI：10.1093/glycob/cwq172

  日期：2011.3

  Sialyl Lewisx (SLex, Siaα2–3Galβ1–4(Fucα1–3)GlcNAcβOR) is an important sialic acid-containing carbohydrate epitope involved in many biological processes such as inflammation and cancer metastasis. In the biosynthetic process of SLex, α2–3-sialyltransferase-catalyzed sialylation generally proceeds prior to α1–3-fucosyltransferase-catalyzed fucosylation. For the chemoenzymatic synthesis of SLex containing different sialic acid forms, however, it would be more efficient if diverse sialic acid forms are transferred in the last step to the fucosylated substrate Lewisx (Lex). An α2–3-sialyltransferase obtained from myxoma virus-infected European rabbit kidney RK13 cells (viral α2–3-sialyltransferase (vST3Gal-I)) was reported to be able to tolerate fucosylated substrate Lex. Nevertheless, the substrate specificity of the enzyme was only determined using partially purified protein from extracts of cells infected with myxoma virus. Herein we demonstrate that a previously reported multifunctional bacterial enzyme Pasteurella multocida sialyltransferase 1 (PmST1) can also use Lex as an acceptor substrate, although at a much lower efficiency compared to nonfucosylated acceptor. In addition, N-terminal 30-amino-acid truncated vST3Gal-I has been successfully cloned and expressed in Escherichia coli Origami™ B(DE3) cells as a fusion protein with an N-terminal maltose binding protein (MBP) and a C-terminal His6-tag (MBP-Δ30vST3Gal-I-His6). The viral protein has been purified to homogeneity and characterized biochemically. The enzyme is active in a broad pH range varying from 5.0 to 9.0. It does not require a divalent metal for its α2–3-sialyltransferase activity. It has been used in one-pot multienzyme sialylation of Lex for the synthesis of SLex containing different sialic acid forms with good yields.

  Sialyl Lewisx（SLex，Siaα2-3Galβ1-4(Fucα1-3)GlcNAcβOR）是一种重要的含硅烷基酸的碳水化合物表位，参与了许多生物过程，如炎症和癌症转移。在 SLex 的生物合成过程中，α2-3-硅氨酰基转移酶催化的硅氨酰化通常先于α1-3-岩藻糖基转移酶催化的岩藻糖基化。然而，对于含有不同硅烷基酸形式的 SLex 的化学酶法合成，如果在最后一步将不同的硅烷基酸形式转移到岩藻糖基化底物 Lewisx（Lex）上，效率会更高。据报道，从受肌瘤病毒感染的欧洲兔肾 RK13 细胞中获得的α2-3-氨酰基转移酶（病毒α2-3-氨酰基转移酶（vST3Gal-I））能够耐受岩藻糖基化底物 Lex。然而，该酶的底物特异性只能通过从感染了肌瘤病毒的细胞提取物中部分纯化的蛋白质来确定。在这里，我们证明了以前报道过的一种多功能细菌酶多杀性巴氏杆菌硅氨基转移酶 1（PmST1）也能使用 Lex 作为接受底物，不过与非岩藻糖基化接受底物相比，其效率要低得多。此外，N-末端 30 氨基酸截短的 vST3Gal-I 已被成功克隆，并在大肠杆菌 Origami™ B(DE3) 细胞中表达为与 N-末端麦芽糖结合蛋白（MBP）和 C-末端 His6 标记（MBP-Δ30vST3Gal-I-His6）的融合蛋白。病毒蛋白已被纯化至均一，并进行了生化鉴定。该酶在 5.0 到 9.0 的广泛 pH 值范围内都具有活性。它的α2-3-糖基转移酶活性不需要二价金属。它已被用于对 Lex 进行单锅多酶硅氨酰化，以合成含有不同硅氨酰形式的 SLex，而且产量很高。
• Azasugar compound
  申请人：Mitsubishi Chemical Corporation

  公开号：US20040147591A1

  公开（公告）日：2004-07-29

  The present invention provides a compound represented by the formula (I) or a salt thereof: 1 wherein R 1 represents a hydrogen atom, a C 1-10 alkyl group optionally having a substituent, or a protecting group of N; R 2 represents a C 1-10 alkyl group optionally having a substituent or a C 2-10 alkenyl group optionally having a substituent; R 3 and R 4 independently represent a hydrogen atom or a protecting group of hydroxyl group; X represents —N(R 5 )R 6 or a residue of amino acid or of an amino group of a peptide wherein R 5 and R 6 independently represent a hydrogen atom, a C 1-10 alkyl group optionally having a substituent, or a C 3-12 cycloalkyl group optionally having a substituent; and Y represents a hydrogen atom, —CH 2 NH 2 , —CONH 2 , or —COOH. The compound of the present invention is useful as a specific inhibitor of sugar chain related enzymes such as glycosyltransferase and glycosidase, and is useful as, for example, a medicine for treating or preventing diseases associated with sugar chain related enzymes.

  本发明提供了一种由式(I)表示的化合物或其盐：1其中，R1表示氢原子，C1-10烷基，可选地具有取代基，或N的保护基; R2表示C1-10烷基，可选地具有取代基，或C2-10烯基，可选地具有取代基; R3和R4分别表示氢原子或羟基的保护基; X表示-N（R5）R6或氨基酸或肽的氨基团的残基，其中R5和R6分别表示氢原子，C1-10烷基，可选地具有取代基，或C3-12环烷基，可选地具有取代基; Y表示氢原子，-CH2NH2，-CONH2或-COOH。本发明的化合物可用作糖链相关酶的特异性抑制剂，例如，用作治疗或预防与糖链相关酶相关的疾病的药物。
• Modified Proteins
  申请人：Behrens Carsten

  公开号：US20080108557A1

  公开（公告）日：2008-05-08

  A method of conjugating peptides and proteins by means of glycosyltransferase is provided.

  提供了一种通过糖基转移酶结合肽和蛋白质的方法。
• Synthesis of 2-[(2-pyridyl)amino]ethyl β-d-lactosaminide and evaluation of its acceptor ability for sialyltransferase: a comparison with 4-methylumbelliferyl and dansyl β-d-lactosaminide
  作者：Yasuhiro Kajihara、Daisuke Kamiyama、Naoki Yamamoto、Tohru Sakakibara、Masayuki Izumi、Hironobu Hashimoto

  DOI：10.1016/j.carres.2004.03.015

  日期：2004.6

  We report the synthesis Of P-D-lactosaminide with a 2-aminopyridyl group that is linked to a glycosyl tether at the reducing end. This fluorescent disaccharide acts as an acceptor for both alpha-(2 --> 6)- and alpha-(2 --> 3)-sialyltransferases. In addition, the acceptor ability of this disaccharide was evaluated and compared with that Of beta-D-lactosaminide having a dansyl or a 4-methylumbelliferyl group. (C) 2004 Elsevier Ltd. All rights reserved.