2,5,10,14-desacetyl taxuyunnanine C | 444578-19-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,5,10,14-desacetyl taxuyunnanine C
• 英文别名: taxa-4(20),11(12)-dien-2α,5α,10β,14β-tetraol；2α,5α,10β,14β-tetrahydroxytaxa-4(20),11-diene；(1S,2S,3S,5S,8S,10S,14S)-8,12,15,15-tetramethyl-4-methylidenetricyclo[9.3.1.03,8]pentadec-11-ene-2,5,10,14-tetrol
• CAS: 444578-19-2
• 化学式: C₂₀H₃₂O₄
• 分子量: 336.472
• InChiKey: UMGMHDKMWHPVMR-UWDSTRGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,5,10,14-desacetyl taxuyunnanine C 在 咪唑 、 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三正丁基氢锡 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 吡啶 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 175.34h， 生成 Taxa-4(20),11(12)-dien-10β-tert-butyldimethylsilyloxy-5α-acetate
  参考文献：
  名称：

  Studies on Taxol Biosynthesis. Preparation of Taxa-4(20),11(12)-dien-5α-acetoxy-10β-ol by Deoxygenation of a Taxadiene Tetraacetate Obtained from Japanese Yew

  摘要：

  Taxa-4(20),11(12)-dien-5alpha-acetoxy-10beta-ol 6 has been identified as an early stage intermediate involved in the biosynthesis of taxol (Paclitaxel). This compound has been efficiently prepared by Barton deoxygenation of the C-2- and C-14-hydroxyl groups on a derivative semisynthetically prepared from taxa-4(20),11(12)-dien-2alpha,5alpha,10beta-triacetoxy-14beta-(2-methyl)butyrate (7), a major taxoid metabolite isolated from Japanese yew heart wood. The synthetic methodology is amenable for the preparation of isotopically labeled congeners that will be useful to probe further intermediate steps in the biosynthesis of taxol.

  DOI：

  10.1021/jo025679z
• 作为产物：
  描述：

  2α,5α,10β-triacetoxy-14β-(2'-methyl)-butysyloxy-4(20),11-taxadiene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 23.0h， 以89%的产率得到2,5,10,14-desacetyl taxuyunnanine C
  参考文献：
  名称：

  Studies on Taxol Biosynthesis. Preparation of Taxa-4(20),11(12)-dien-5α-acetoxy-10β-ol by Deoxygenation of a Taxadiene Tetraacetate Obtained from Japanese Yew

  摘要：

  Taxa-4(20),11(12)-dien-5alpha-acetoxy-10beta-ol 6 has been identified as an early stage intermediate involved in the biosynthesis of taxol (Paclitaxel). This compound has been efficiently prepared by Barton deoxygenation of the C-2- and C-14-hydroxyl groups on a derivative semisynthetically prepared from taxa-4(20),11(12)-dien-2alpha,5alpha,10beta-triacetoxy-14beta-(2-methyl)butyrate (7), a major taxoid metabolite isolated from Japanese yew heart wood. The synthetic methodology is amenable for the preparation of isotopically labeled congeners that will be useful to probe further intermediate steps in the biosynthesis of taxol.

  DOI：

  10.1021/jo025679z

文献信息

• Microbial transformations of taxadienes and the multi-drug resistant tumor reversal activities of the metabolites
  作者：Xiao Liu、Ridao Chen、Dan Xie、Mei Mei、Jianhua Zou、Xiaoguang Chen、Jungui Dai

  DOI：10.1016/j.tet.2012.09.091

  日期：2012.11

  Microbial transformation of two taxadienes (1, 2) was individually investigated with two filamentous fungi, Cunninghamella echinulata CGMCC 3.3400 and Aspergillus niger CGMCC 3.1858, and two actinomycete stains, Streptomyces griseus CACC 200300 and Nocardia purpurea CGMCC 4.1182. A total of 21 products were obtained, 13 of which were new compounds. The reactions that occurred exhibited diversity, including

  2个taxadienes（微生物转化1，2）中的溶液单独地具有两个丝状真菌研究，小克银汉霉刺孢小克CGMCC 3.3400和黑曲霉CGMCC 3.1858，以及两个放线菌的污渍，灰色链霉菌CACC 200300和诺卡氏菌菊CGMCC 4.1182。总共获得21种产品，其中13种是新化合物。发生的反应表现出多样性，包括选择性羟基化，环氧化，氧化，脱甲基，乙酰化，脱乙酰基和O-烷基化，我们提出了可行的生物转化途径。药理评估的结果表明，化合物15与10μM紫杉醇共同给药时，对多药耐药性（MDR）肿瘤细胞系A549 /紫杉醇具有明显的逆转活性。这项研究提供了一种有用的方法来制备新的活性紫杉烷衍生物，这些衍生物很难通过化学手段获得。
• Special publicationfn1fn1Papers with this heading have received accelerated publication, due to their particular significance in the field of phytochemistry. Purification and characterization of acetyl coenzyme a: 10-hydroxytaxane O-acetyltransferase from cell suspension cultures of Taxus chinensis
  作者：Birgitta Menhard、Meinhart H Zenk

  DOI：10.1016/s0031-9422(98)00674-8

  日期：1999.3

  An O-acetyltransferase that catalyzes the regiospecific acetylation of a range of taxanes possessing an unsubstituted 10-hydroxyl group was detected and purified to apparent electrophoretic homogeneity from a cytosolic fraction of Taxus chinensis cell cultures. The purification involved negative calcium phosphate adsorption, sephadex desalting, DEAE, AcA44 chromatography, HighQ, CHT II, HiTrap Blue, Phenylsepharose and Mimetic Green purification steps. The purified acetyltransferase was found to be a monomeric protein of 71 +/- 1.5 kDa that is highly regio- and stereospecific towards the 10 beta-hydroxyl group of the taxane molecule and is also active towards 10-desacetylbaccatine III. The acetyltransferase reaction had a pH optimum of 9.0 with halfmaximal activities at pH 6.8 and 10.8, respectively. The temperature optimum was at 35 degrees C and the isoelectric point at 5.6. The apparent K-m values for 10-desacetyltaxuyunnanine C and acetyl CoA were 23 and 61 mu M, respectively. The turnover rate for the enzyme using both substrates was 0.2 mol mol(-1) of enzyme. The kinetic optimum was determined to be K-cat/K-m = 8.7 s(-1) L M-1. (C) 1999 Elsevier Science Ltd. All rights reserved.