Summary
The thioester, N,S-diacetylcysteine, is formed during the illumination of phosphate buffered (pH 7.0) aqueous solutions of acetaldehyde and N,N′-diacetylcystine with ultraviolet light. The yield of N,S-diacetylcysteine relative to N-acetylcysteine and unidentified products progressively increases as ultraviolet light below 239 nm, 253 nm and 281 nm is cut off with optical filters. When ultraviolet light below 320 nm is removed with an optical filter, there is no detectable reaction. Illumination of 0.025 M N,N′-diacetylcystine with 0.5 M and 1.0 M acetaldehyde with filtered ultraviolet light gives, respectively, 20% and 80% yields of N,S-diacetylcysteine. In the reaction with 1.0 M acetaldehyde, N-acetylcysteine forms early in the reaction and later decreases with its conversion to N,S-diacetylcysteine. The prebiotic significance of these reactions is discussed.
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Abbreviations
- Ac-Cys:
-
N-acetylcysteine
- Ac-Cys(Ac):
-
N,S-diacetylcysteine
- Ac-Cys:
-
N,N′-diacetylcystine
References
Asquith RS, Shah AV (1971) Biochim Biophys Acta 244:547–556
Berkner LV, Marshall LC (1965) J Atmos Sci 22:225–261
Bridger WA (1974) Succinyl-CoA Synthetase. In: Boyer PD (ed) The Enzymes, vol X. Academic Press, New York, p 581
Broda E (1975) The Evolution of Bioenergetic Processes. Pergamon Press, Oxford, p 43
Bruice TC, Benkovic SJ (1966) Bioorganic Mechanisms, vol 1. Benjamin, New York, p 259
Buvet R (1978) Compared Energetics of Primordial and Biological Metabolisms. In: Noda H (ed) Origin of Life. Japan Scientific Societies Press, Tokyo, p 411
Calvert JG, Pitts JN Jr (1966) Photochemistry. Wiley, New York, p 368
DiSabato G, Jencks WP (1961) J Am Chem Soc 83:4400–4405
Egami F (1974) Orig Life 5:405–413
Fluharty AL (1974) Biochemistry of the Thiol Group. In: Patai S (ed) The Chemistry of the Thiol Group. Wiley, London, p 589
Goldman P, Vagelos PR (1964) Acyl-Transfer Reactions (CoA-Structure, Function). In: Florkin M, Stotz EH (eds) Comprehensive Biochemistry, vol 15. Elsevier, Amsterdam, p 71
Grassetti DR, Murray JF Jr (1969) J Chromatogr 41:121–123
Harris JI, Waters M (1976) Glyceraldehyde-3-Phosphate Dehydrogenase. In: Boyer PD (ed) The Enzymes, 3rd edn, vol XIII. Academic Press, New York, p 1
Hart MH (1979) Origins of Life 9:261–266
Hartman H (1975) J Mol Evol 4:359–370
Hollander L, DuVigneaud V (1931) J Biol Chem 94:243–252
Hong JH, Becker RS (1979) J Mol Evol 13:15–26
Hulshof J, Ponnamperuma C (1976) Origins of Life 7:197–224
Jencks WP (1976) Free Energies of Hydrolysis and Decarboxylation. In: Fasman GD (ed) Handbook of Biochemistry and Molecular Biology, 3rd edn. Physical and Chemical Data, vol I. CRC Press, Cleveland, p 296
Jocelyn PC (1972) Biochemistry of the SH Group. Academic Press, New York, p 50
Knight AR (1974) Photochemistry of Thiols. In: Patai S (ed) The Chemistry of the Thiol Group. Wiley, New York, p 455
Lorand L, Stenberg P (1976) Endo-γ-Glutamine: ε-Lysine Trans-ferases Enzymes Which Cross-link Proteins. In: Fasman GD (ed) Handbook of Biochemistry and Molecular Biology, 3rd edn. Proteins, vol II. CRC Press, Cleveland, p 669
Miller SL (1957) Ann NY Acad Sci 69:260–275
Ochiai EI (1978) Origins of Life 9:81–91
Oro J, Stephen-Sherwood E (1976) Orig Life 7:37–47
Pitts JN Jr, Wan JKS (1966) Photochemistry of Ketones and Aldehydes. In: Patai S (ed) The Chemistry of the Carbonyl Group. Wiley, New York, p 823
Raulin F (1978) Incorporation of Sulfur in Chemical Evolution. In: Noda H (ed) Origin of Life. Japan Scientific Societies Press, Tokyo, p 177
Risi S, Dose K, Rathinasamy TK, Augenstein L (1967) Photochem Photobiol 6:423–436
Sagan C, Khare BN (1971) Science 173:417–420
Slater EC (1966) Oxidative Phosphorylation. In: Florkin M, Stotz EH (eds) Comprehensive Biochemistry, vol 14. Elsevier, Amsterdam, p 327
Smith HA, Gorin G (1961) J Org Chem 26:820–823
Stadtman ER (1952) J Biol Chem 196:535–546
Stadtman ER (1957) Preparation and Assay of Acyl Coenzyme A and Other Thioesters; Use of Hydroxylamine. In: Colowick SP, Kaplan NO (eds) Methods in Enzymology, vol III. Academic Press, New York, p 931
Stirling CJM (1958) J Chem Soc 4524–4530
Takagi M, Goto S, Matsuda T (1976) J Chem Soc Chem Commun 92–93
Zahler WL, Cleland WW (1968) J Biol Chem 243:716–719
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Weber, A.L. Formation of the thioester, N,S-diacetylcysteine, from acetaldehyde and N,N′diacetylcystine in aqueous solution with ultraviolet light. J Mol Evol 17, 103–107 (1981). https://doi.org/10.1007/BF01732680
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DOI: https://doi.org/10.1007/BF01732680