192
Views
1
CrossRef citations to date
0
Altmetric
Articles

Asymmetric synthesis of (S,R)- and (R,R)-methiin stereoisomers

, , &
Pages 713-717 | Received 03 Feb 2020, Accepted 26 Mar 2020, Published online: 29 Apr 2020

References

  • Rose, P.; Whiteman, M.; Moore, P. K.; Yi, Z. Z. Bioactive S-Alk(en)yl Cysteine Sulfoxide Metabolites in the Genus Allium: The Chemistry of Potential Therapeutic Agents. Nat. Prod. Rep. 2005, 22, 351–368. DOI: 10.1039/b417639c.
  • Morris, C. J.; Thompson, J. F. The Identification of (+)-S-Methyl-L-Cysteine Sulfoxide in Plants. J. Am. Chem. Soc. 1956, 78, 1605–1608. DOI: 10.1021/ja01589a028.
  • Marks, H. S.; Hilson, J. A.; Leichtweis, H. C.; Stoewsand, G. S. S-Methylcysteine Sulfoxide in Brassica Vegetables and Formation of Methyl Methanethiosulfinate from Brussels Sprouts. J. Agric. Food Chem. 1992, 40, 2098–21012. DOI: 10.1021/jf00023a012.
  • Krest, I.; Glodek, J.; Keusgen, M. Cysteine Sulfoxides and Alliinase Activity of Some Allium Species. J. Agric. Food Chem. 2000, 48, 3753–3760.
  • Stoewsand, G. S. Bioactive Organosulfur Phytochemicals in Brassica Oleracea Vegetables-a Review. Food Chem. Toxicol. 1995, 33, 537–543. DOI: 10.1016/0278-6915(95)00017-V.
  • Sugii, M.; Suzuki, T.; Kakimoto, T.; Kato, J. Studies on the Sulfur-Containing Amino Acids and the Related Compounds in Garlic. (I): Assimilation of Sulfate [³5S] in GarlicBull. Inst. Chem. Res. 1964, 42, 246.
  • Kristensen, I.; Larsen, P. O.; Sørensen, H. Free Amino Acids and γ-Glutamyl Peptides in Seeds of Fagus sylvatica. Phytochemistry 1974, 13, 2803–2811. DOI: 10.1016/0031-9422(74)80245-1.
  • Alabran, D. A.; Mabrouk, A. F. Carrot Flavor. Sugars and Free Nitrogenous Compounds in Fresh Carrots. J. Agric. Food Chem. 1973, 21, 205–208. DOI: 10.1021/jf60186a020.
  • Bielinska-Czarnecka, M. Ninhydrin-Reacting Substances from Apple Spurs. J. Sci. Food Agric. 1963, 14, 527–528. DOI: 10.1002/jsfa.2740140716.
  • McKee, H. S.; Urbach, G. E. The Physiology of Growth in Apple Fruits. Aust. J. Bio. Sci. 1953, 6, 369–378. DOI: 10.1071/BI9530369.
  • Steward, F. C.; Hulme, A. C.; Freiberg, S. R.; Hegarty, M. P.; Pollard, J. K.; Rabson, R.; Barr, R. A. Physiological Investigations on the Banana Plant: With Nine Figures in the Text: Biochemical Constituents Detected in the Banana. Plant Ann. Bot. 1960, 24, 83–87. DOI: 10.1093/oxfordjournals.aob.a083691.
  • Lancaster, J. E.; Shaw, M. L.; Walton, E. F. S-Alk(en)yl-l-Cysteine Sulfoxides, Alliinase and Aroma in Leucocoryne. Phytochemistry 2000, 55, 127–130. DOI: 10.1016/S0031-9422(00)00245-4.
  • Keusgen, M.; Junger, M.; Krest, I.; Schoning, M. J. Development of a Biosensor Specific for Cysteine Sulfoxides. Biosensors Bioelectron. 2003, 18, 805–812. DOI: 10.1016/S0956-5663(03)00045-9.
  • Higuchi, O.; Tateshita, K.; Nishimura, H. Antioxidative Activity of Sulfur-Containing Compounds in Allium Species for Human Low-Density Lipoprotein (LDL) Oxidation in Vitro. J. Agric. Food Chem. 2003, 51, 7208–7214. DOI: 10.1021/jf034294u.
  • Itokawa, Y.; Inoue, K.; Sasagawa, S.; Fujiwara, M. Effect of S-Methylcysteine Sulfoxide, S-Allylcysteine Sulfoxide and Related Sulfur-Containing Amino Acids on Lipid Metabolism of Experimental Hypercholesterolemic Rats. J. Nutr 1973, 103, 88–92. DOI: 10.1093/jn/103.1.88.
  • Lowson, L. D. Bioactive Organosulfur Compounds of Garlic and Garlic Products Role in Reducing Blood Lipids Human Medicinal Agents from Plants. Presented at the ACS Symposium Series. Vol. 534, 306–330. Chapter 21, 1993.
  • Helen, A.; Krishnakumar, K.; Vijayammal, P. L.; Augusti, K. T. A Comparative Study of Antioxidants S-Allyl Cysteine Sulfoxide and Vitamin E on the Damages Induced by Nicotine in Rats. Pharmacology 2003, 67, 113–117. DOI: 10.1159/000067796.
  • Augusti, K. T.; Sheela, C. G. Antiperoxide Effect of S-Allyl Cysteine Sulfoxide, an Insulin Secretagogue, in Diabetic Rats. Experientia 1996, 52, 115–119. DOI: 10.1007/BF01923354.
  • Kanwar, T.; Roy, A.; Prasad, P. Management of Diabetes and Complication: Herbal Therapies. UK J. Pharm. Biosci. 2017, 5, 51–59. DOI: 10.20510/ukjpb/5/i5/166557.
  • Holland, H. L.; Brown, F. M.; Lozada, D.; Mayne, B.; Szerminski, W. R.; van Vliet, A. J. Chloroperoxidase-Catalyzed Oxidation of Methionine Derivatives. Can. J. Chem. 2002, 80, 633–639. DOI: 10.1139/v02-025.
  • Holland, H. L.; Brown, F. M.; Johnson, D. V.; Kerridge, A.; Mayne, B.; Turner, C. D.; Vliet, A. J. Biocatalytic Oxidation of S-Alkylcysteine Derivatives by Chloroperoxidase and Beauveria Species. J. Mol. Catal. B: Enzym. 2002, 17, 249–256. DOI: 10.1016/S1381-1177(02)00041-3.
  • Hibi, M.; Kawashima, T.; Yajima, H.; Smirnov, S. V.; Kodera, T.; Sugiyama, M.; Shimizu, S.; Yokozeki, K.; Ogawa, J. Enzymatic Synthesis of Chiral Amino Acid Sulfoxides by Fe(II)/α-Ketoglutarate-Dependent Dioxygenase. Tetrahedron: Asymmetry 2013, 24, 990–994. DOI: 10.1016/j.tetasy.2013.07.017.
  • Loginova, I. V.; Rubtsova, S. A.; Kuchin, A. V. Oxidation by Chlorine Dioxide of Methionine and Cysteine Derivatives to Sulfoxides. Chem. Nat. Compd. 2008, 44, 752–754. DOI: 10.1007/s10600-009-9182-8.
  • Meese, C.; Specht, D.; Hofmann, U. Syntheses of Metabolites of S-Carboxymethyl-L-Cysteine and S-Methyl-L-Cysteine and of Some Isotopically Labelled (2H,13C) Analogues. Arch. Pharm. Pharm. Med. Chem. 1990, 323, 957–965. DOI: 10.1002/ardp.19903231205.
  • Synge, R. L. M.; Wood, J. C. (+)-(S-Methyl-L-Cysteine S-Oxide) in Cabbage. Biochem. J. 1956, 64, 252–259. DOI: 10.1042/bj0640252.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.