An experimental study of the low-temperature sulfurization of carbohydrates

Organic Geochemistry

Volumn 34, Issue 8, 2003, Pages 1129-1144

  Van Dongen, Bart E ^a,c   Schouten, Stefan ^a   Baas, Marianne ^a   Geenevasen, Jan A J ^b   Sinninghe Damsté, Jaap S ^a  

^a ROYAL NETHERLANDS INSTITUTE FOR SEA RESEARCH   (Netherlands)

^b UNIVERSITY OF AMSTERDAM   (Netherlands)

^c UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATES; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

SULFURIZATION;

GEOCHEMISTRY;

CARBOHYDRATE; LOW TEMPERATURE; ORGANIC GEOCHEMISTRY; ORGANIC MATTER; SULFUR;

EID: 0042066677     PISSN: 01466380     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0146-6380(03)00060-3     Document Type: Article

References (43)

1. 13C-NMR spectra of alditols. Carbohydrate Research 84, 201-209.
2. Arnosti, C., 1995. Measurement of depth- and site-related differences in polysaccharide hydrolysis rates in marine sediments. Geochim. Cosmochim. Acta 59, 4247-4257.
3. Arnosti, C., Repeta, D., 1994. Oligosaccharide degradation by anaerobic marine bacteria: characterization of an experimental system to study polymer degradation in sediments. Limnol. Oceanogr. 39, 1865-1877.
4. Arnosti, C., Repeta, D.J., Blough, N.V., 1994. Rapid bacterial degradation of polysaccarides in anoxic marine systems. Geochim. Cosmochim. Acta 58, 2639-2652.
5. Brassell, S.C., Lewis, C.A., de Leeuw, J.W., de Lange, F., Sinninghe Damsté, J.S., 1986. Isoprenoid thiophenes: novel products of sediment diagenesis? Nature 320, 160-162.
6. Eglinton, T.I., Aluwihare, L.I., Bauer, J.E., Druffel, E.R.M., McNichol, A.P., 1996. Gas chromatographic isolation of individual compounds from complex matrices for radiocarbon dating. Anal. Chem. 68, 904-912.
7. Eglinton, T.I., Sinninghe Damsté, J.S., Kohnen, M.E.L., de Leeuw, J.W., 1990a. Rapid estimation of the organic sulphur content of kerogens, coals and asphaltenes by pyrolysis-gas chromatography. Fuel 69, 1394-1404.
8. Eglinton, T.I., Sinninghe Damsté, J.S., Kohnen, M.E.L., de Leeuw, J.W., Larter, S.R., Patience, R.L., 1990b. Analysis of maturity-related changes in the organic sulfur composition of kerogens by flash pyrolysis-gas chromatography. In: Orr, W.L., White, C.M. (Eds.), Geochemistry of Sulfur in Fossil Fuels: American Chemical Society, Washington, DC, pp. 529-565.
9. El Khadem, H.S., Ennifar, S., Isbell, H.S., 1987. Contribution of reactions pathways involved in the izomerization of monosaccharides by alkali. Carbohydrate Research 169, 13-21.
10. Eliel, E.L., Hutchins, R.O., Mebane, R., Willer, R.L., 1976. Endocyclic vs. exocyclic attack in nucleophilic displacement reactions on five- and six-membered cyclic onium salts. J. Org. Chem. 41, 1052-1057.
11. Harsch, G., Bauer, H., Voelter, W., 1984. Kinctik, Katalyse und Mechanismus der Sekundärreaktion in der Schlussphase der Formose-Reaktion. Liebigs Annalen der Chemie 623-834.
12. Jarosz, S., Skóra, S., Szewcyk, K., Ciunik, Z., 2001. Reaction of sugar allyltins with aldehydes. A remarkable difference in reactivity between furanose and pyranose organometallic derivatives. Tetrahedron: Asymmetry 12, 1895-1905.
13. Kamerling, J.P., Vliegenthart, F.G., 1974. Carbohydrates. In: Curtius, H.Ch., Roth, M. (Eds.), Clinical Biochemistry - Principles and Methods. Walter de Gruyter, Berlin/New York, pp. 175-263.
14. Kamo, T., Hirai, N., Iwami, K., Fujioka, D., Ohigashi, H., 2001. New phenylphenalenones from banana fruit. Tetrahedron 57, 7649-7656.
15. Klok, J., Nieberg-van Velzen, E.H., de Leeuw, J.W., Schenck, P.A., 1981. Capillary gas chromatography separation of monosaccharides as their alditol acetates. J. Chromatogr. 207, 273-275.
16. Kohnen, M.E.L., Sinninghc Damsté, J.S., Kock-van Dalen, A.C., de Leeuw, J.W., 1991. Di- or polysulphide-bound biomarkers in sulphur-rich geomacromolecules as revealed by selective chemolysis. Geochim. Cosmochim. Acta 55, 1375-1394.
17. 30 highly branched isoprenoid sulphur compounds: further evidence for the formation of organic sulphur compounds during early diagenesis. Geochim. Cosmochim. Acta 54, 3053-3063.
18. Kok, M.D., Rijpstra, W.I.C., Robertson, L., Volkman, J.K., Sinninghe Damsté, J.S., 2000a. Early steroid sulfurisation in surface sediments of a permanently stratified lake (Ace Lake, Antarctica). Geochim. Cosmochim. Acta 64, 1425-1436.
19. Kok, M.D., Schouten, S., Sinninghe Damsté, J.S., 1995. Laboratory simulation of natural sulphurization: the reactivity of some functionalized model compounds and the catalytic influence of sediment. In: Grimalt, J.O., Dorronsoro, C. (Eds.), Organic Geochemistry: Developments and Applications to Energy, Climate, Environment and Human History. Donostia-San Sebastián, The Basque Country, pp. 1047-1049.
20. Kok, M.D., Schouten, S., Sinninghe Damsté J.S., 2000b. Formation of insoluble, nonhydrolyzable, sulfur-rich macromolecules via incorporation of inorganic sulfur species into algal carbohydrates. Geochim. Cosmochim. Acta 64, 2689-2699.
21. Krein, E.B., Aizenshtat, Z., 1994. The formation of isoprenoid sulfur compounds during diagenesis: simulated sulfur incorporation and thermal transformation. Org. Geochem 21, 1015-1025.
22. Moers, M.E.C., Boon, J.J., de Leeuw, J.W., Baas, M., Schenck, P.A., 1989. Carbohydrate speciation and Py-MS mapping of peat samples from a subtropical open marsh environment. Geochim. Cosmochim. Acta 53, 2011-2021.
23. Orr, W.L., 1986. Kerogen/asphaltene/sulfur relationships in sulphur-rich Monterey oils. Org. Geochem 10, 499-516.
24. Orr, W.L., Sinninghe Damsté, J.S., 1990. Geochemistry of sulfur in petroleum systems: introduction and overview. ACS Symp. Ser. 429, 2-29.
25. Osawa, E., Imai, K., Fujiyoshi-Yoneda, T., Jaime, C., 1991. On the possibility of determining stereochemistry in acyclic polyhydroxylated compounds by the combined vicinal coupling constant/molecular mechanics method. A test with alditol peracetates. Tetrahedron 47, 4579-4590.
26. Schneckenburger, P., Adam, P., Albrecht, P., 1998. Thioketones as key intermediates in the reduction of ketones to thiols by HS in natural environments. Tetrahedron Letters 39, 447-450.
27. Schouten, S., de Graaf, W., Sinninghe Damsté, J.S., van Driel, G.B., de Leeuw, J.W., 1993. Laboratory simulation of natural sulphurization: II. Reaction of multi-functionalized lipids with inorganic polysulphides at low temperatures. Org. Geochem. 22, 825-834.
28. Schouten, S., van Driel, G.B., Sinninghe Damsté, J.S., de Leeuw, J.W., 1994. Natural sulphurization of ketones and aldehydes: a key reaction in the formation of organic sulphur compounds. Geochim. Cosmochim. Acta 58, 5111-5116.
29. Sinninghe Damsté, J.S., de Leeuw, J.W., 1990. Analysis, structure and geochemical significance of organically-bound sulphur in the geosphere: state of the art and future research. In: Durand, B., Behar, F. (Eds.), Advances in Organic Geochemistry, 1989. Pergamon Press, Oxford, pp. 1077-1101.
30. Sinninghe Damsté, J.S., de Leeuw, J.W., 1992. Organically bound sulphur in coal: a molecular approach. Fuel Processing Technology 30, 109-178.
31. Sinninghe Damsté, J.S., Kock-van Dalen, A.C., de Leeuw, J.W., Schenck, P.A., 1988. Identification of homologous series of alkylated thiophenes, thiolanes, thianes, and benzothiophenes present in pyrolysates of sulphur-rich kerogens. J. Chromatogr 435, 435-452.
32. Sinninghe Damsté, J.S., Kohnen, M., Horsfield, B., 1998a. Origin of low-molecular-weight alkylthiophenes in pyrolysates of sulphur-rich kerogens as revealed by micro-scale vessel pyrolysis. Org. Geochem 29, 1891-1903.
33. Sinninghe Damsté, J.S., Kok, M.D., Köster, J., Schouten, S., 1998b. Sulfurized carbohydrates: an important sedimentary sink for organic carbon? Earth and Planetary Science Letters 164, 7-13.
34. Sinninghe Damsté, J.S., Rijpstra, W.I.C., Kock-van Dalen, A.C., de Leeuw, J.W., Schenck, P.A., 1989. Quenching of labile functionalised lipids by inorganic sulphur species: evidence for the formation of sedimentary organic sulphur compounds at the early stages of diagenesis. Geochim. Cosmochim. Acta 53, 1343-1355.
35. Sinninghe Damsté, J.S., van Dongen, B.E., Rijpstra, W.I.C., Schouten, S., Volkman, J.K., Geenevasen, J.A.J., 2001. Novel intact glycolipids in sediments from an Antarctic lake (Ace Lake). Org. Geochem 32, 321-332.
36. Sinninghe Damsté, J.S., White, C.M., Green, J.B., de Leeuw, J.W., 1999. Organosulfur compounds in sulfur-rich Rasa coal. Energ. Fuel 13, 728-738.
37. Stock, L.M., Wolny, R., Bal, B., 1989. Sulfur distribution in American bituminous coals. Energ. Fuel 3, 651-461.
38. Ten Haven, H.L., Rullkötter, J., Sinninghe Damsté, J.S., de Leeuw, J.W., 1990. Distribution of organic sulphur compounds in Mesozoic and Cenozoic sediments from the Atlantic and Pacific Oceans and the Gulf of California. In: Orr, W.L., White, C.M. (Eds.), Geochemistry of Sulfur in Fossil Fuels. ACS Symp. Series 429. American Chemical Society, Washington, DC, pp. 613-632.
39. 35 hopanoid in sediments. Tetrahedron Letters 25, 1163-1183.
40. van Dongen, B.E., Schoulen, S., Sinninghe Damsté, J.S., 2002. Carbon isotope variability in monosaccharides and lipids of aquatic and terrestrial plants. Mar. Ecol-Prog. Ser, 232, 83-92.
41. van Kaam-Peters, H.M.E., Schouten, S., Köster, J., Sinninghe Damsté, J.S., 1998. Controls on the molecular and carbon isotopic composition of organic matter deposited in a Kimmeridgian euxinic shelf sea: evidence for preservation of carbohydrates through sulfurisation. Geochimica et Cosmochimica Acta 62, 3259-3283.
42. Wakeham, S.G., Sinninghe Damsté, J.S., Kohnen, M.E.L., de Leeuw, J.W., 1995. Organic sulfur compounds formed during early diagenesis in Black Sea sediments. Geochimica et Cosmochimica Acta 59, 521-533.
43. Werne, J.P., Hollander, D.J., Behrens, A., Schaeffer, P., Albrecht, P., Sinninghe Damsté, J.S., 2000. Timing of early diagenetic sulfurization of organic matter: a precursor-product relationship in Holocene sediments of the anoxic Cariaco Basin, Venezuela. Geochimica et Cosmochimzieca Acta 64, 1741-1751.