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5'-AMP的化学酯化主要发生在2'位。

Chemical esterification of 5'-AMP occurs predominantly at the 2' position.

作者信息

Lacey J C, Thomas R D, Wickaramasinghe N S, Watkins C L

机构信息

Department of Biochemistry, University of Alabama, Birmingham 35294.

出版信息

J Mol Evol. 1990 Oct;31(4):251-6. doi: 10.1007/BF02101120.

DOI:10.1007/BF02101120
PMID:2175365
Abstract

We describe experiments here which show that chemical esterification of 5'-adenylic acid (5'-AMP) with N-acetyl D- or L-phenylalanine (Ac-D- or Ac-L-Phe) imidazolide occurs principally, if not exclusively, at the 2' position. Furthermore, in experiments with the formation of the 2'-3' diester with butyric acid and N-acetyl glycine (Ac-Gly), we found the second esterification was also predominantly at the 2' position. This means that mixed diesters can be predictably prepared with the positions of the substituents known. The results are consistent with a model for the preferential catalytic synthesis of L-based peptides via a 2'-3' diester intermediate of purine monoribonucleotides.

摘要

我们在此描述的实验表明，5'-腺苷酸（5'-AMP）与N-乙酰基-D-或-L-苯丙氨酸（Ac-D-或Ac-L-Phe）咪唑化物的化学酯化反应主要（如果不是唯一的话）发生在2'位。此外，在与丁酸和N-乙酰甘氨酸（Ac-Gly）形成2'-3'二酯的实验中，我们发现第二次酯化反应也主要发生在2'位。这意味着可以可预测地制备出取代基位置已知的混合二酯。这些结果与通过嘌呤单核糖核苷酸的2'-3'二酯中间体优先催化合成L型肽的模型一致。

相似文献

1
Chemical esterification of 5'-AMP occurs predominantly at the 2' position.5'-AMP的化学酯化主要发生在2'位。
J Mol Evol. 1990 Oct;31(4):251-6. doi: 10.1007/BF02101120.
2
Esterification of all four monoribonucleotides with acetyl-D-L-valine proceeds with a preference for the D-isomer but the D/L ratio in the products declines as a function of the hydrophobicity of the nucleotide.所有四种单核糖核苷酸与乙酰-D-缬氨酸的酯化反应对D-异构体有偏好，但产物中的D/L比率会随着核苷酸疏水性的增加而下降。
Bioorg Chem. 1992;20:265-8. doi: 10.1016/0045-2068(92)90019-y.
3
Stereoselective formation of bis(alpha-aminoacyl) esters of 5'-AMP suggests a primitive peptide synthesizing system with a preference for L-amino acids.5'-AMP的双（α-氨基酰基）酯的立体选择性形成表明存在一种对L-氨基酸有偏好的原始肽合成系统。
Biochim Biophys Acta. 1991 Feb 15;1076(3):395-400. doi: 10.1016/0167-4838(91)90482-f.
4
Differential distribution of D and L amino acids between the 2' and 3' positions of the AMP residue at the 3' terminus of transfer ribonucleic acid.转运核糖核酸3'末端AMP残基2'和3'位置之间D型和L型氨基酸的差异分布。
Proc Natl Acad Sci U S A. 1988 Jul;85(14):4996-5000. doi: 10.1073/pnas.85.14.4996.
5
Mixed anhydrides (phosphoric-carboxyl) are also formed in the esterification of 5'-AMP with N-acetylaminoacyl imidazolides: implications regarding the origin of protein synthesis.在5'-腺苷一磷酸与N-乙酰氨基酰咪唑化物的酯化反应中也会形成混合酸酐（磷酸-羧基）：关于蛋白质合成起源的启示。
Orig Life Evol Biosph. 1992;22:361-8. doi: 10.1007/BF01809372.
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Preferential hydrophobic interactions are responsible for a preference of D-amino acids in the aminoacylation of 5'-AMP with hydrophobic amino acids.
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7
N-Acetyl-D- and L-esters of 5'-AMP hydrolyze at different rates.5'-AMP的N-乙酰-D-酯和L-酯以不同速率水解。
Chirality. 1993;5:150-3. doi: 10.1002/chir.530050308.
8
Self-association and protonation of adenosine 5'-monophosphate in comparison with its 2'- and 3'-analogues and tubercidin 5'-monophosphate (7-deaza-AMP).5'-单磷酸腺苷与其2'-和3'-类似物以及5'-单磷酸杀结核菌素（7-脱氮-AMP）的自缔合和质子化作用比较
Eur J Biochem. 1987 Mar 2;163(2):353-63. doi: 10.1111/j.1432-1033.1987.tb10807.x.
9
Aminoacyl-nucleotide reactions: studies related to the origin of the genetic code and protein synthesis.氨酰核苷酸反应：与遗传密码起源和蛋白质合成相关的研究
Orig Life. 1984;14(1-4):597-604. doi: 10.1007/BF00933709.
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Kinetic analysis of three activated phenylalanyl intermediates generated by the initiation module PheATE of gramicidin S synthetase.短杆菌肽S合成酶起始模块PheATE生成的三种活化苯丙氨酰中间体的动力学分析。
Biochemistry. 2001 May 8;40(18):5329-37. doi: 10.1021/bi015518+.

引用本文的文献

1
Mixed anhydrides (phosphoric-carboxyl) are also formed in the esterification of 5'-AMP with N-acetylaminoacyl imidazolides: implications regarding the origin of protein synthesis.在5'-腺苷一磷酸与N-乙酰氨基酰咪唑化物的酯化反应中也会形成混合酸酐（磷酸-羧基）：关于蛋白质合成起源的启示。
Orig Life Evol Biosph. 1992;22:361-8. doi: 10.1007/BF01809372.
2
Catalytic roles of the AMP at the 3' end of tRNAs.转运RNA 3' 末端腺苷单磷酸的催化作用。
Mol Cell Biochem. 1994 Oct 26;139(2):117-21. doi: 10.1007/BF01081734.
3
Ribonucleic acids may be catalysts for the preferential synthesis of L-amino acid peptides: a minireview.

本文引用的文献

1
Hydrolytic properties of phenylalanyl- and N-acetylphenylalanyl adenylate anhydrides.苯丙氨酰和N-乙酰苯丙氨酰腺苷酸酐的水解特性。
Orig Life Evol Biosph. 1984;15(1):45-54. doi: 10.1007/BF01809392.
2
Transacylation rates of (aminoacyl)adenosine moiety at the 3'-terminus of aminoacyl transfer ribonucleic acid.氨酰基转移核糖核酸3'末端（氨酰基）腺苷部分的转酰基化速率。
Biochemistry. 1983 Jun 21;22(13):3220-5. doi: 10.1021/bi00282a028.
3
Stereoselective aminoacylation of a dinucleoside monophosphate by the imidazolides of DL-alanine and N-(tert-butoxycarbonyl)-DL-alanine.
核糖核酸可能是L-氨基酸肽优先合成的催化剂：一篇综述。
J Mol Evol. 1990 Sep;31(3):244-8. doi: 10.1007/BF02109502.
4
Preferential hydrophobic interactions are responsible for a preference of D-amino acids in the aminoacylation of 5'-AMP with hydrophobic amino acids.
Experientia. 1992 Apr 15;48(4):379-83. doi: 10.1007/BF01923434.
5
Experimental studies on the origin of the genetic code and the process of protein synthesis: a review update.遗传密码的起源与蛋白质合成过程的实验研究：综述更新
Orig Life Evol Biosph. 1992;22(5):243-75. doi: 10.1007/BF01810856.
DL-丙氨酸和N-（叔丁氧羰基）-DL-丙氨酸的咪唑酯对二磷酸核苷进行立体选择性氨酰化反应。
J Mol Evol. 1984;20(2):147-56. doi: 10.1007/BF02257375.
4
Experimental studies related to the origin of the genetic code and the process of protein synthesis--a review.关于遗传密码起源和蛋白质合成过程的实验研究——综述
Orig Life. 1983 Mar;13(1):3-42. doi: 10.1007/BF00928761.
5
The general synthetic route to amino acid esters of nucleotides and nucleoside-5'-triphosphates and some properties of these compounds.核苷酸和核苷 -5'-三磷酸的氨基酸酯的一般合成路线以及这些化合物的一些性质。
Tetrahedron. 1970 Sep;26(18):4419-33. doi: 10.1016/s0040-4020(01)93090-x.
6
Slow transacylation of peptidyladenosine allows analysis of the 2'/3'-isomer specificity of peptidyltransferase.
Biochemistry. 1985 Oct 8;24(21):5776-80. doi: 10.1021/bi00342a013.
7
Chirally selective, intramolecular interaction observed in an aminoacyl adenylate anhydride.在氨酰腺苷酸酐中观察到的手性选择性分子内相互作用。
Orig Life Evol Biosph. 1985;16(2):151-6. doi: 10.1007/BF01809468.
8
Differential distribution of D and L amino acids between the 2' and 3' positions of the AMP residue at the 3' terminus of transfer ribonucleic acid.转运核糖核酸3'末端AMP残基2'和3'位置之间D型和L型氨基酸的差异分布。
Proc Natl Acad Sci U S A. 1988 Jul;85(14):4996-5000. doi: 10.1073/pnas.85.14.4996.
9
Aliphatic amino acid side chains associate with the "face" of the adenine ring.脂肪族氨基酸侧链与腺嘌呤环的“面”缔合。
J Biomol Struct Dyn. 1986 Feb;3(4):783-93. doi: 10.1080/07391102.1986.10508461.
10
The polymerization of amino acid adenylates on sodium-montmorillonite with preadsorbed polypeptides.氨基酸腺苷酸在预先吸附有多肽的钠蒙脱石上的聚合反应。
Orig Life Evol Biosph. 1988;18(4):359-87. doi: 10.1007/BF01808216.