Prebiotic Phosphate Ester Syntheses in a Deep Eutectic Solvent

被引：51

作者：

Gull, Maheen ^{[1
]}

Zhou, Manshui ^{[2
]}

Fernandez, Facundo M. ^{[2
]}

Pasek, Matthew A. ^{[1
]}

机构：

[1] Univ S Florida, Sch Geosci, Tampa, FL 33620 USA

[2] Georgia Inst Technol, Sch Chem & Biochem, Atlanta, GA 30332 USA

来源：

JOURNAL OF MOLECULAR EVOLUTION | 2014年 / 78卷 / 02期

关键词：

Prebiotic synthesis; Phosphorylation; Origin of life; Deep eutectic solvents; Phosphate esters; PHOSPHORYLATION; PHOSPHORUS; ORIGIN; STRUVITE; ACID;

D O I：

10.1007/s00239-013-9605-9

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

We report a route to synthesize a wide range of organophosphates of biological significance in a deep eutectic solvent (2: 1 urea and choline chloride), utilizing various orthophosphate sources. Heating an organic alcohol in the solvent along with a soluble phosphorus source yields phosphorus esters of choline as well as that of the added organic in yields between 15 to 99 %. In addition, phosphite analogs of biological phosphates and peptides were also formed by the simple mixing of reagents and heating at 60-70 degrees C in the deep eutectic solvent. The presented dehydration reactions are relevant to prebiotic and green chemistry in alternative solvents.

引用

收藏

页码：109 / 117

页数：9

相关论文

共 39 条

[1] Glycerol eutectics as sustainable solvent systems [J].

Abbott, Andrew P. ;

Harris, Robert C. ;

Ryder, Karl S. ;

D'Agostino, Carmine ;

Gladden, Lynn F. ;

Mantle, Mick D. .

GREEN CHEMISTRY, 2011, 13 (01) :82-90

[2] Deep eutectic solvents formed between choline chloride and carboxylic acids: Versatile alternatives to ionic liquids [J].

Abbott, AP ;

Boothby, D ;

Capper, G ;

Davies, DL ;

Rasheed, RK .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (29) :9142-9147

[3] Novel solvent properties of choline chloride/urea mixtures [J].

Abbott, AP ;

Capper, G ;

Davies, DL ;

Rasheed, RK ;

Tambyrajah, V .

CHEMICAL COMMUNICATIONS, 2003, (01) :70-71

[4] Entropy and charge in molecular evolution - the case of phosphate [J].

Arrhenius, G ;

Sales, B ;

Mojzsis, S ;

Lee, T .

JOURNAL OF THEORETICAL BIOLOGY, 1997, 187 (04) :503-522

[5] Prebiotic synthesis of vitamin B6-type compounds [J].

Austin, SM ;

Waddell, TG .

ORIGINS OF LIFE AND EVOLUTION OF THE BIOSPHERE, 1999, 29 (03) :287-296

[6] Why did Nature select phosphate for its dominant roles in biology? [J].

Bowler, Matthew W. ;

Cliff, Matthew J. ;

Waltho, Jonathan P. ;

Blackburn, G. Michael .

NEW JOURNAL OF CHEMISTRY, 2010, 34 (05) :784-794

[7] Direct evidence for the availability of reactive, water soluble phosphorus on the early Earth. H-Phosphinic acid from the Nantan meteorite [J].

Bryant, David E. ;

Kee, Terence P. .

CHEMICAL COMMUNICATIONS, 2006, (22) :2344-2346

[8] On the prebiotic potential of reduced oxidation state phosphorus: the H-phosphinate-pyruvate system [J].

Bryant, David E. ;

Marriott, Katie E. R. ;

Macgregor, Stuart A. ;

Kilner, Colin ;

Pasek, Matthew A. ;

Kee, Terence P. .

CHEMICAL COMMUNICATIONS, 2010, 46 (21) :3726-3728

[9] Phosphorylation of adenosine with trimetaphosphate under simulated prebiotic conditions [J].

Cheng, CM ;

Fan, C ;

Wan, R ;

Tong, CY ;

Miao, ZW ;

Chen, J ;

Zhao, YF .

ORIGINS OF LIFE AND EVOLUTION OF THE BIOSPHERE, 2002, 32 (03) :219-224

[10] Are Natural Deep Eutectic Solvents the Missing Link in Understanding Cellular Metabolism and Physiology? [J].

Choi, Young Hae ;

van Spronsen, Jaap ;

Dai, Yuntao ;

Verberne, Marianne ;

Hollmann, Frank ;

Arends, Isabel W. C. E. ;

Witkamp, Geert-Jan ;

Verpoorte, Robert .

PLANT PHYSIOLOGY, 2011, 156 (04) :1701-1705

← 1 2 3 4 →