ethyl 9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine-6-carbamate | 33422-70-7

分子结构分类

有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷

中文名称

——

中文别名

——

英文名称

ethyl 9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine-6-carbamate

英文别名

N⁶-(ethoxycarbonyl)-2',3',5'-tri-O-acetyladenosine；[9-(tri-O-acetyl-β-D-ribofuranosyl)-9H-purin-6-yl]-carbamic acid ethyl ester；O^2'_,O3'_,O5'-triacetyl-N⁶-ethoxycarbonyl-adenosine；N-(Ethoxycarbonyl)-adenosine；[(2R,3R,4R,5R)-3,4-diacetyloxy-5-[6-(ethoxycarbonylamino)purin-9-yl]oxolan-2-yl]methyl acetate

ethyl 9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine-6-carbamate化学式

CAS

33422-70-7

化学式

C₁₉H₂₃N₅O₉

mdl

——

分子量

465.42

InChiKey

FKCCKGOMRHXEOL-SCFUHWHPSA-N

BEILSTEIN

——

EINECS

——

物化性质

溶解度：

可溶于乙酸乙酯;甲醇

计算性质

辛醇/水分配系数(LogP)：

0.2
重原子数：

33
可旋转键数：

11
环数：

3.0
sp3杂化的碳原子比例：

0.53
拓扑面积：

170
氢给体数：

1
氢受体数：

12

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
2',3',5'-三乙酰腺苷	triacetyladenosine	7387-57-7	C₁₆H₁₉N₅O₇	393.356
——	N6-(1-ethoxy-2-chloroethylidene)-2',3',5'-tri-O-acetyladenosine	96394-56-8	C₂₀H₂₄ClN₅O₈	497.892
——	8-ethoxy-3-(2',3',5'-tri-O-acetylribofuranosyl)imidazo<2,1-i>purine	96394-53-5	C₂₀H₂₃N₅O₈	461.431
腺苷	adenosine	58-61-7	C₁₀H₁₃N₅O₄	267.244

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	N-[9-(tri-O-acetyl-β-D-ribofuranosyl)-purin-6-ylcarbamoyl]-glycine	56893-28-8	C₁₉H₂₂N₆O₁₀	494.418
——	(2,3,5-tri-O-acetyl-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl])-L-threonine	56893-27-7	C₂₁H₂₆N₆O₁₁	538.471
——	(2,3,5-tri-O-acetyl-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl])-O-tert-butyldimethylsilyl-L-threonine	292053-90-8	C₂₇H₄₀N₆O₁₁Si	652.734
——	(2R,3R,4R,5R)-2-(acetoxymethyl)-5-(6-(3-((5R,6S)-2,2,3,3,5,9,9,10,10-nonamethyl-7-oxo-4,8-dioxa-3,9-disilaundecan-6-yl)ureido)-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate	292053-96-4	C₃₃H₅₄N₆O₁₁Si₂	766.996
——	(2,3,5-tri-O-acetyl-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl])-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester	292053-97-5	C₃₂H₅₂N₆O₁₁Si₂	752.969
N-[[(9-beta-D-呋喃核糖基-9H-嘌呤-6-基)氨基]羰基]-L-苏氨酸	N⁶-threonylcarbamoyladenosine	24719-82-2	C₁₅H₂₀N₆O₈	412.359
——	N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester	292053-91-9	C₂₆H₄₆N₆O₈Si₂	626.858
——	5'-O-(4,4'-dimethoxytrityl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester	292053-99-7	C₄₇H₆₄N₆O₁₀Si₂	929.23
——	5'-O-(4,4'-dimethoxytrityl)-3'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester	292054-00-3	C₅₃H₇₈N₆O₁₀Si₃	1043.49
——	5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N-[(9-β-D-ribofuranosyl-9H-purin-6-yl)carbamoyl]-O-tert-butyldimethylsilyl-L-threonine 2-trimethylsilylethyl ester	292053-98-6	C₅₃H₇₈N₆O₁₀Si₃	1043.49

反应信息

作为反应物：

描述：

ethyl 9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine-6-carbamate 在吡啶、氨作用下，以甲醇为溶剂，反应 16.0h，生成

参考文献：

名称：

在假定的 RNA 肽世界中将氨基酸加载到 RNA 上

摘要：

在假定的生命起源前 RNA 肽世界中，用氨基酸装载 RNA 是朝着基于 RNA 的肽合成迈出的第一步。报道了结合N-甲基氨基甲酰基核苷酸和一系列氨基酸的RNA 链的有效加载。加载的 RNA 链也经历了基于 RNA 的氨基酸转移反应。

DOI：

10.1002/anie.202302360
作为产物：

描述：

N6-(1-ethoxy-2-chloroethylidene)-2',3',5'-tri-O-acetyladenosine 在间氯过氧苯甲酸作用下，以二氯甲烷、 N,N-二甲基甲酰胺为溶剂，反应 8.0h，生成 ethyl 9-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-9H-purine-6-carbamate

参考文献：

名称：

Nucleoside annelating reagents: N-(tert-butoxycarbonyl)-2-bromoacetamide and 2-chloroketene diethyl acetal

摘要：

DOI：

10.1021/jo00214a015

点击查看最新优质反应信息

文献信息

Noncanonical RNA Nucleosides as Molecular Fossils of an Early Earth-Generation by Prebiotic Methylations and Carbamoylations

作者：Christina Schneider、Sidney Becker、Hidenori Okamura、Antony Crisp、Tynchtyk Amatov、Michael Stadlmeier、Thomas Carell

DOI：10.1002/anie.201801919

日期：2018.5.14

prebiotic routes towards RNA. Contemporary RNA, however, is not only constructed from the four canonical nucleobases (A, C, G, and U), it also contains many chemically modified (noncanonical) bases. A still open question is whether these noncanonical bases were formed in parallel to the canonical bases (chemical origin) or later, when life demanded higher functional diversity (biological origin). Here

RNA世界假说假设地球上的生命始于催化其自身形成的小RNA分子。对该假设至关重要的是，需要针对RNA的益生元途径。然而，当代RNA不仅由四个规范的核碱基（A，C，G和U）构建，而且还包含许多化学修饰的（非规范）碱基。一个尚待解决的问题是，当生命需要更高的功能多样性（生物起源）时，这些非规范碱基是否与规范碱基（化学起源）平行或更晚地形成。在这里，我们显示异氰酸酯与亚硝酸钠的组合建立了与地球早期条件相容的甲基化和氨基甲酰化反应性。这些反应导致仍然存在的甲基化和氨基酸修饰的核苷的形成。
Synthesis and Characterization of the Native Anticodon Domain of E. coli tRNALys: Simultaneous Incorporation of Modified Nucleosides mnm5s2U, t6A, and Pseudouridine Using Phosphoramidite Chemistry

作者：Mallikarjun Sundaram、Pamela F. Crain、Darrell R. Davis

DOI：10.1021/jo000338b

日期：2000.9.1

protecting groups suitable for automated RNA oligonucleotide synthesis. The 17 nucleotide anticodon stem-loop of E. coli tRNA(Lys) was then assembled from these synthons using phosphoramidite coupling chemistry. Coupling efficiencies for the two hypermodified nucleosides and for pseudouridine phosphoramidite were all greater than 98%. A mild deprotection scheme was developed to accommodate the highly functionalized

大肠杆菌tRNA（Lys）的反密码子结构域分别在位置34和37处包含超修饰的核苷mnm（5）s（2）U和t（6）A，以及在位置39处更常见的psi。这三个核苷酸中的一个代表自然界中最广泛修饰的RNA结构域之一。高度修饰的核苷mnm（5）s（2）U和t（6）A的2-氰乙基二异丙基亚磷酰胺分别带有适合于自动RNA寡核苷酸合成的保护基。然后使用亚磷酰胺偶联化学从这些合成子组装大肠杆菌tRNA（Lys）的17个核苷酸的反密码子茎环。两种超修饰核苷和假尿苷亚磷酰胺的偶联效率均大于98％。开发了温和的脱保护方案以容纳高度官能化的RNA。高偶联产率，温和的脱保护作用以及高效的HPLC纯化使我们能够从1微摩尔规模的RNA合成物中获得1. 8 mg的纯化RNA。我们有效的合成方案将允许对该独特的tRNA物种进行生物物理研究，其中已显示核苷修饰在密码子-反密码子识别，tRNA氨酰基合成酶识别和程序化核糖体移码
Stability studies on the newly discovered cyclic form of tRNA N6-threonylcarbamoyladenosine (ct6A)

作者：Michal Matuszewski、Elzbieta Sochacka

DOI：10.1016/j.bmcl.2014.04.048

日期：2014.6

A cyclic form of N-6-threonylcarbamoyladenosine bearing an oxazolone moiety (ct(6)A) was discovered very recently at the position 37 in several tRNA sequences. Our study on the synthesized 5',3',2'-O-acetylated derivative of ct(6)A confirmed high stability of the modified nucleoside under physiological conditions (PBS buffer, pH 7.4) and revealed remarkable stability of the oxazolone ring in acidic (100 mM HCl, pH 1) and basic (0.1 mM NaOH, pH 10) conditions. This feature may allow for the post-synthetic conversion of t(6)A into ct(6)A in assembled oligoribonucleotides. (C) 2014 Elsevier Ltd. All rights reserved.