尿嘧啶多氧菌素 C | 24695-48-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 中文名称: 尿嘧啶多氧菌素 C
• 中文别名: 尿嘧啶多氧菌素C
• 英文名称: 1-(5'-amino-5'-deoxy-α-D-allofuranuronosyl)uracil
• 英文别名: (2S)-2-amino-2-[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]acetic acid
• CAS: 24695-48-5
• 化学式: C₁₀H₁₃N₃O₇
• 分子量: 287.229
• InChiKey: OTBZTPBBZITZBP-TVNFTVLESA-N

物化性质

• 熔点：
  241-245 °C
• 密度：
  1.782±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  162
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  尿嘧啶多氧菌素 C 在 sodium hydroxide 、 sodium tetrahydroborate 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 1-<5'-(benzylmethylamino)-5'-deoxy-β-D-allofuranosyluronic acid>uracil
  参考文献：
  名称：

  Angiotensin converting enzyme inhibitors. (Mercaptoaroyl)amino acids

  摘要：

  A series of (mercaptoaroyl)amino acids and related compounds was synthesized and tested for ability to inhibit angiotensin converting enzyme (ACE). The most active compound was N-(3-chloro-2-mercaptobenzoyl)-N-cyclopentylglycine, having an in vitro I50 = 0.28 microM. Substitution of the aromatic 3-position by small polar groups enhanced ACE inhibitory activity, whereas bulky groups diminished it. Alteration of the beta relationship between the mercaptan and amide carbonyl or masking of the thiol by acylation reduced activity. Replacement of the thiol by nitro, hydroxy, or carboxy gave compounds lacking ACE inhibitory activity.

  DOI：

  10.1021/jm00381a012
• 作为产物：
  描述：

  neopolyoxin C 在 sodium hydroxide 作用下， 生成 尿嘧啶多氧菌素 C
  参考文献：
  名称：

  Structures of neopolyoxins A, B, and C

  摘要：

  DOI：

  10.1016/s0040-4039(00)78698-9

文献信息

• (1-Ethoxyvinyl)lithium in the Total Synthesis Thymine Polyoxin C and Uracil Polyoxin C.
  作者：Hiroyuki AKITA、Kimio UCHIDA、Cheng Yu CHEN、Keisuke KATO

  DOI：10.1248/cpb.46.1034

  日期：——

  A short path synthesis of the ethyl (methyl 2, 3-O-isopropylidene-β-D-allofuranosid)uronate (5) and ethyl(methyl 2, 3-O-isopropylidene-α-L-talofuranosid)uronate (6) from methyl 2, 3-O-isopropylidene-β-D-ribopentodialdo-1, 4-furanoside (3) using (1-ethoxyvinyl)lithium and its application to the total synthesis of the pyrimidine nucleosides, thymine polyoxin C (1) and uracil polyoxin C (2), are described.

  描述了一种短步骤合成的方法，通过使用(1-乙氧基乙烯)锂，将甲基2, 3-O-异丙烯基-β-D-阿洛呋喃苷(3)转化为乙基(甲基2, 3-O-异丙烯基-β-D-阿洛呋喃糖尿酸酯)(5)和乙基(甲基2, 3-O-异丙烯基-α-L-塔罗呋喃糖尿酸酯)(6)，并将其应用于胸腺嘧啶多抗生素C (1)和尿嘧啶多抗生素C (2)的总合成。
• Chemistry of the neopolyoxins, pyrimidine and imidazoline nucleoside peptide antibiotics
  作者：Masakazu Uramoto、Kimie Kobinata、Kiyoshi Isono、Tsutomu Higashijima、Tatsuo Miyazawa、Ellen E. Jenkins、James A. McCloskey

  DOI：10.1016/0040-4020(82)80135-x

  日期：1982.1

  and C were isolated from the culture filtrate of Streptomyces cacaoi subsp. asoensis. Their absolute structures have been established on the basis of chemical and spectroscopic evidence. They are structural analogs of the polyoxins. As a nucleobase, neopolyoxin C possesses uracil, while neopolyoxins A and B contain the imidazoline moiety. A ring contraction reaction of pyrimidine nucleoside into imidazoline

  从可食链霉菌亚种的培养滤液中分离出新的几丁质合成酶抑制剂，新多恶菌素A，B和C。麻生太郎。它们的绝对结构是根据化学和光谱学证据确定的。它们是多氧合蛋白的结构类似物。作为多核新毒素C的核碱基，它具有尿嘧啶，而新多毒素A和B含有咪唑啉部分。嘧啶核苷到咪唑啉核苷的环收缩反应在核苷部分的结构确定中起关键作用。有人建议对新多毒素A和B的生物合成进行类似的转化。
• Synthesis of uracil polyoxin C from uridine
  作者：Claude Mvondo Evina、Georges Guillerm

  DOI：10.1016/0040-4039(95)02116-7

  日期：1996.1

  An improved procedure is reported for the asymmetric synthesis of uracil polyoxin C (UPOC) from 2′,3′-O-isopropylideneuridine-5′-aldehyde. The methodology described here is based on the highly diastereocontrolled formation of 1-(β-D-allofuranosyl)uracil and its facile conversion into the corresponding 2,5′-O-cyclouridine derivative, a key step for the sterocontrolled formation of the terminal α-amino

  据报道，从2'，3'- O-异丙基亚氨基尿嘧啶-5'-醛不对称合成尿嘧啶多氧合蛋白C（UPOC）的方法有所改进。此处描述的方法基于1-（β-D-氟呋喃糖基）尿嘧啶的高度非对映体控制形成及其轻松转化为相应的2,5'- O-环尿苷衍生物，这是对端基α进行立体控制形成的关键步骤-UPOC的氨基酸。
• Novel nikkomycin analogues: inhibitors of the fungal cell wall biosynthesis enzyme chitin synthase
  作者：Kikoh Obi、Jun-ichiro Uda、Kazuhiko Iwase、Osamu Sugimoto、Hiroyuki Ebisu、Akira Matsuda

  DOI：10.1016/s0960-894x(00)00256-0

  日期：2000.7

  A series of novel nikkomycin analogue inhibitors of the chitin synthase of fungal cell wall was synthesized and evaluated for their inhibitory activities. Among them, the compound having a phenanthrene group at the terminal amino acid was found to possess strong anti-chitin synthase activity.

  合成了一系列新颖的真菌细胞壁几丁质合酶尼古霉素类似物抑制剂，并对其抑制活性进行了评估。其中，发现在末端氨基酸具有菲基的化合物具有强的抗甲壳质合酶活性。
• Applications of crotyldiisopinocampheylboranes in synthesis: the total synthesis of nikkomycin B
  作者：Anthony G. M. Barrett、Suzanne A. Lebold

  DOI：10.1021/jo00016a014

  日期：1991.8

  (-)-(E)-Crotyldiisopinocampheylborane was employed in a highly diastereoselective and enantioselective synthesis of the gamma-hydroxy-beta-methyl-alpha-aminobutanoic acid moiety of nikkomycin B. A protected derivative of this N-terminal amino acid residue was condensed with uracil polyoxin C benzyl ester to provide, on deprotection, the antifungal agent nikkomycin B.

  (-)-(E)-肉豆蔻二异莰基硼烷被用于尼可霉素B中γ-羟基-β-甲基-α-氨基丁酸片段的高对映选择性和非对映选择性合成。该N端氨基酸残基的保护衍生物与尿嘧啶聚氧嘧啶C苄酯发生缩合反应，经去保护后可获得抗真菌剂尼可霉素B。