Prebiotic chemistry of phosphonic acids: Products derived from phosphonoacetaldehyde in the presence of formaldehyde

被引：15

作者：

De Graaf, RM ^{[1
]}

Visscher, J ^{[1
]}

Schwartz, AW ^{[1
]}

机构：

[1] Univ Nijmegen, Fac Sci, Evolut Biol Res Grp, NL-6500 GL Nijmegen, Netherlands

来源：

ORIGINS OF LIFE AND EVOLUTION OF THE BIOSPHERE | 1998年 / 28卷 / 03期

基金：

美国国家航空航天局;

关键词：

Polymer; Formaldehyde; HPLC; Geochemistry; Building Block;

D O I：

10.1023/A:1006543225618

中图分类号：

Q [生物科学];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Phosphonoacetaldehyde (PAL), a phosphonic acid analogue of glycolaldehyde phosphate, reacts in the presence of formaldehyde under mildly basic conditions to produce several new products. The reaction proceeds in two stages: a fast aldol condensation of formaldehyde with PAL, and a slower reaction to produce products containing two phosphonic acid groups. We report on the derivatization, isolation by means of HPLC and characterization of these compounds. One of the products is of potential interest as a building block for a prebiotic informational polymer.

引用

页码：271 / 282

页数：12

共 11 条

[1] ALKYL PHOSPHONIC-ACIDS AND SULFONIC-ACIDS IN THE MURCHISON METEORITE [J].

COOPER, GW ;

ONWO, WM ;

CRONIN, JR .

GEOCHIMICA ET COSMOCHIMICA ACTA, 1992, 56 (11) :4109-4115

[2] A PLAUSIBLY PREBIOTIC SYNTHESIS OF PHOSPHONIC-ACIDS [J].

DEGRAAF, RM ;

VISSCHER, J ;

SCHWARTZ, AW .

NATURE, 1995, 378 (6556) :474-477

[3] Reactive phosphonic acids as prebiotic carriers of phosphorus [J].

DeGraaf, RM ;

Visscher, J ;

Schwartz, AW .

JOURNAL OF MOLECULAR EVOLUTION, 1997, 44 (03) :237-241

[4] DETERMINATION OF MONOSACCHARIDES IN GLYCOPROTEINS BY REVERSE-PHASE HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY [J].

KWON, H ;

KIM, J .

ANALYTICAL BIOCHEMISTRY, 1993, 215 (02) :243-252

[5] THE MECHANISM OF SYNTHESIS OF AMINO ACIDS BY ELECTRIC DISCHARGES [J].

MILLER, SL .

BIOCHIMICA ET BIOPHYSICA ACTA, 1957, 23 (03) :480-489

[6]

MOUREY D, 1981, ORIGIN LIFE

[7] CHEMISTRY OF ALPHA-AMINONITRILES - ALDOMERISATION OF GLYCOLALDEHYDE PHOSPHATE TO RAC-HEXOSE 2,4,6-TRIPHOSPHATES AND (IN PRESENCE OF FORMALDEHYDE) RAC-PENTOSE 2,4-DIPHOSPHATES - RAC-ALLOSE 2,4,6-TRIPHOSPHATE AND RAC-RIBOSE 2,4-DIPHOSPHATE ARE THE MAIN REACTION-PRODUCTS [J].

MULLER, D ;

PITSCH, S ;

KITTAKA, A ;

WAGNER, E ;

WINTNER, CE ;

ESCHENMOSER, A .

HELVETICA CHIMICA ACTA, 1990, 73 (05) :1410-1468

[8] WHY PENTOSE-NUCLEIC AND NOT HEXOSE-NUCLEIC ACIDS .7. PYRANOSYL-RNA (P-RNA) [J].

PITSCH, S ;

WENDEBORN, S ;

JAUN, B ;

ESCHENMOSER, A .

HELVETICA CHIMICA ACTA, 1993, 76 (06) :2161-2183

[9] THE PREBIOTIC SYNTHESIS OF CARBOHYDRATES - A REASSESSMENT [J].

SCHWARTZ, AW ;

DEGRAAF, RM .

JOURNAL OF MOLECULAR EVOLUTION, 1993, 36 (02) :101-106

[10] Speculation on the RNA precursor problem [J].

Schwartz, AW .

JOURNAL OF THEORETICAL BIOLOGY, 1997, 187 (04) :523-527

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