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Volumn , Issue 14, 2008, Pages 2161-2163

Potentially prebiotic passerini-type reactions of phosphates

Author keywords

Multicomponent reactions; Passerini reaction; Phosphates; Phosphorylation; Prebiotic chemistry

Indexed keywords

CARBOXYLIC ACID; PHOSPHATE; PREBIOTIC AGENT;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PH; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 51149120394 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078018 Document Type: Article

Times cited : (10)

References (10)

1
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- Baldwin, J. E.; Chan, R. Y.; Sutherland, J. D. Tetrahedron Lett. 1994, 35, 5519.
- (1994) Tetrahedron Lett , vol.35 , pp. 5519
- Baldwin, J.E.¹ Chan, R.Y.² Sutherland, J.D.³

2
- 35649000936
- Mullen, L. B.; Sutherland, J. D. Angew. Chem. Int. Ed. 2007, 46, 8063.
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 8063
- Mullen, L.B.¹ Sutherland, J.D.²

3
- 27444436849
- Pirrung, M. C.; Das Sarma, K. Tetrahedron 2005, 61, 11456.
- (2005) Tetrahedron , vol.61 , pp. 11456
- Pirrung, M.C.¹ Das Sarma, K.²

4
- 50849087128
- Subsequent to our demonstration that alkyl phosphates can act as organocatalysts of the three-component Ugi reaction ref. 2, List has identified phenyl phosphinic acid 'as the best catalyst for this perfectly atom-economic reaction, thus introducing a new motif for organocatalysis, Pan, S. C, List, B. Angew. Chem. Int. Ed. 2008, 47, 3622
- Subsequent to our demonstration that alkyl phosphates can act as organocatalysts of the three-component Ugi reaction (ref. 2), List has identified phenyl phosphinic acid 'as the best catalyst for this perfectly atom-economic reaction, thus introducing a new motif for organocatalysis': Pan, S. C.; List, B. Angew. Chem. Int. Ed. 2008, 47, 3622.

5
- 51149124156
- Glycolaldehyde phosphate disodium salt 8 (55 mg, 0.3 mmol) was dissolved in D2O (3 mL) and the pD was adjusted to 6 using NaOD-DCl solution. Methyl isonitrile (18 μL 0.3 mmol) was then added and the solution stirred at r.t. overnight. Data for 11 1HNMR (500 MHz, D 2O, δ, 2.73 (s, 3 H, CH3, 3.96 (ddd, J, 11.4, 7.3, 5.0 Hz, 1 H, CHHOP, 4.02 (ddd, J, 11.0, 6.3, 2.8 Hz, 1 H, CHHOP, 4.25 (app. t, J, 4.1, 3.8 Hz, 1 H, CHOH, 13C NMR (75 MHz, D2O, δ, 25.6 (CH3, 66.3 (CH2OP, 71.6 (CHOH, 174.3 (CONHCH3, 31P NMR (81 MHz, D2O, δ, 1.32 t, J, 6.4 Hz
- 2O): δ = 1.32 (t, J = 6.4 Hz).

6
- 0014403644
- (a) Ferris, J. P. Science 1968, 161, 53.
- (1968) Science , vol.161 , pp. 53
- Ferris, J.P.¹

7
- 0004874129
- (b) Ferris, J. P.; Goldstein, G.; Beaulieu, D. J. J. Am. Chem. Soc. 1970, 92, 6598.
- (1970) J. Am. Chem. Soc , vol.92 , pp. 6598
- Ferris, J.P.¹ Goldstein, G.² Beaulieu, D.J.³

8
- 0034600774
- Krishnamurthy, R.; Guntha, S.; Eschenmoser, A. Angew. Chem. Int. Ed. 2000, 39, 2281.
- (2000) Angew. Chem. Int. Ed , vol.39 , pp. 2281
- Krishnamurthy, R.¹ Guntha, S.² Eschenmoser, A.³

9
- 51149097967
- Glycolaldehyde 19 (15 mg, 0.25 mmol) and disodium cyanovinylphosphate (18, 145 mg, 0.75 mmol) were dissolved in D 2O (3 mL) and the pD was adjusted to 6 using NaOD-DCl solution. Methyl isonitrile (14 μL, 0.25 mmol) was then added and the solution stirred at r.t. overnight. Data for 20 1H NMR (500 MHz, D 2O, δ, 2.74 (s, 3 H, CH3, 3.81 (dd, J, 12.0, 3.2 Hz, 1 H, CHHOH, 3.85 (dd, J, 12.3, 2.8 Hz, 1 H, CHHOH, 4.44 (app. dt, J, 9.6, 3.2, 2.8 Hz, 1 H, CHOP, 13C NMR (75 MHz, D2O, δ, 25.7 (CH3, 63.3 (CH2OH, 75.2 (CHOP, 31P NMR (81 MHz, D 2O, δ, 2.14 (d, J, 8.9 Hz, ESI-MS: m/z, 198 (87, M, HRMS: m/z calcd for C4H 9O6NP [M, 198.0173; found: 198.0181. Data for 21 1H NMR 500 MHz, D2O
- +].

10
- 51149116871
- 1H NMR analysis because of (partial) hydrogen-deuterium exchange.
- 1H NMR analysis because of (partial) hydrogen-deuterium exchange.

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