Table 1 Substrates investigated in the phosphorylation reaction.

From: Phosphorylation in liquid sulfur dioxide under prebiotically plausible conditions

Substrate

Potential products

Products confirmed by co-injection

Yield (%)

5′ AMPa

ADPb, c

5′ ADP

5′ ADP: (2.0 ± 0.3)

 

ATPc

5′ ATP

5′ ATP: (0.4 ± 0.2)

5′ ADPa

AMPc

5′ AMP

5′ AMP: (68.8 ± 3.7)

 

ATPc

5′ ATP

5′ ATP: (1.1 ± 0.1)

Aa

AMPc

5′/3′/2′ AMP

5′ AMP: (26.7 ± 6.7)

 

ADPc

5′ ADP

5′ ADP: (2.2 ± 0.1)

 

ATP

 

Traces

Ga

GMPc

5′ GMP

5′ GMP: (7.1 ± 1.6)

 

GDPc

5′ GDP

Traces

 

GTP

 

Traces

Ca

CMPc

5′ CMP

5′ CMP: (23.2 ± 2.4)

 

CDPc

5′ CDP

5′ CDP: (3.0 ± 0.3)

 

CTP

 

Traces

Ua

UMPc

5′ UMP

5′ UMP: (29.6 ± 2.5)

 

UDPc

5′ UDP

5′ UDP: (1.5 ± 0.0)

 

UTP

 

Traces

dAa

dAMP

 

Traces

dGa

dGMP

 

Traces

dCa

dCMPc

5′ dCMP

5′ dCMP: (32.6 ± 5.5)

 

dCDPc

5′ dCDP

n. d.d

 

dCTPc

5′ dCTP

Traces

dTa

dTMPc

5′ dTMP

5′ dTMP: (31.7 ± 9.4)

 

dTDPc

5′ dTDP

5′ dTDP: (3.6 ± 0.2)

 

dTTPc

5′ dTTP

Traces

GL

GL phosphatee

GL-1-phosphate, GL-2-phosphate

n. d.c

 

Cyclic GL phosphate

 

n. d.c

 

GL phosphonate

 

n. d.c

 

GL2 phosphate

 

n. d.c

 

GL2 diphosphate

 

n. d.c

 

GL2 triphosphate

 

n. d.c

 

GL3 triphosphate

 

n. d.c

 

Mixed (non-)cyclic GL diphosphate

 

n. d.c

 

Mixed GL2 (non-)cyclic diphosphate

 

n. d.c

GA

GA phosphate

 

n. d.c

 

GA phosphonate

 

n. d.c

 

GA2 phosphonate

 

n. d.c

Rib

Rib phosphatee

Rib-5-phosphate

n. d.c

Sodium Lc

Lc phosphate

 

n. d.c

 

Cyclic Lc phosphate

 

n. d.c

 

Lc phosphonate

 

n. d.c

 

Lc phosphate phosphonate

 

n. d.c

 

Lc triphosphonate

 

n. d.c

 

Lc2 phosphate

 

n. d.c

Ser

Ser phosphatee

O-phospho Ser

n. d.c

 

Ser phosphonate

 

n. d.c

 

Ser diphosphate

 

n. d.c

 

Ser2 phosphate

 

n. d.c

 

Ser2 diphosphate

 

n. d.c

 

Ser triphosphate

 

n. d.c

 

Ser triphosphonate

 

n. d.c

  1. Substrates (100 mM, 1.0 eq.) were phosphorylated with H3PO3 (3.0 eq.) in the presence of urea (1.0 eq.) for 7 d. Yield errors refer to ± s.d. and were obtained by double determination via CE.
  2. aComplete product mixture is displayed in Supplementary Data 1.
  3. bFor bold labelled products, at least one signal was assigned to a particular isomer by co-injection with a reference.
  4. cCE measurement with co-injection.
  5. dNot determined.
  6. eCE-MS measurement with co-injection.