Table 1.

The amphiphile precursors, amino acids + peptides, metabolites, nucleosides, nucleotides and sugars phosphorylated by imidazole phosphate under paste conditions (see SI Section S6).

	Nucleophile	Nucleophile (mmol)	Calcium imidazole phosphate (mmol)	T (°C)	Duration (h)	Yield (%)
Amphiphile precursor	Glycerol	0.65	0.13	50	167	24% Glycerol-1-phosphate 14% Glycerol-2-phosphate (6% Glycerol-1,2-cyclic phosphate)a
Amino acids + peptides	Serine	0.65	0.13	50	46	17% O-phosphoserine
	SerOMe	0.65	0.13	50	169	9% O-phosphoserine 2% O-phosphoserine methyl ester
	ThrOMe	0.65	0.13	50	48	7% O-phosphothreonine
	Ser-His	0.33	0.13	50	46	6% O-phosphoSer-His
Metabolites	Glycerate (Ca2+ salt)	0.65	0.13	50	167	26% 2-Phosphoglycerate 8% 3-Phosphoglycerate
	Glycerate (Na+ salt)	0.65	0.13	50	23	9% 2-Phosphoglycerate 16% 3-Phosphoglycerate
	Lactate (Na+ salt)	0.65	0.13	50	24	10% 2-Phospholactate
	Glycolate (Na+ salt)	0.65	0.13	50	24	31% 2-Phosphoglycolate
	Lactamide	0.65	0.13	50	167	11% Phospholactamide 7% Pyrophospholactamide
Nucleosides	Adenosine	0.65	0.13	50	22	2% A-5′-MP
	Cytidine	0.65	0.13	50	93	7% C-2′-MP 4% C-3′-MP 3% C-5′-MP
	Guanosine	0.65	0.13	50	93	1% G-5′-MP
	Uridine	0.65	0.13	50	22	11% U-5′-MP 7% U-3′-MP
Nucleotides	AMP	0.65	0.13	50	4	20% ADP
	ADP	0.65	0.13	50	0b	18% ATP
	CMP	0.65	0.13	50	5	4% CDP
	CDP	0.65	0.13	50	4	12% CTP
	GMP	0.65	0.13	50	4	15% GDP
	GDP	0.65	0.13	50	0b	18% GTP
	UMP	0.65	0.13	50	4	4% UDP
	UDP	0.65	0.13	50	0b	25% UTP
Sugars	d-Ribose	0.65	0.13	50	23	69%c
	d-Glucose	0.65	0.13	50	24	70%c
	d-Glucose	0.65	0.13	50	48	33%c

^aThe formation of Glycerol-1,2-cyclic phosphate was observed after 24 h. However, this signal disappeared after heating for 167 h (see Supplementary Fig. 65).

^bt = 0 h is after drying to paste.

^cFor ribose and glucose, multiple peaks in the ³¹P-NMR spectra for phosphorylated sugars were observed (see Supplementary Fig. 135–143). The yield quoted is the summation of integrals from all of these peaks.