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Volumn 56, Issue 10, 2008, Pages 3758-3763

Synthesis of the individual diastereomers of the cysteine conjugate of 3-mercaptohexanol (3-MH)

Author keywords

3 MH; Aroma, flavor; Cysteine conjugates; Thiols; Wine

Indexed keywords

3 MERCAPTOHEXANOL; 3-MERCAPTOHEXANOL; CYSTEINE; HEXANOL; THIOL DERIVATIVE;

EID: 45549090562     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf8000444     Document Type: Article
Times cited : (44)

References (28)
  • 1
    • 0034625484 scopus 로고    scopus 로고
    • Analysis of organic sulfur compounds in wine aroma
    • Mestres, M.; Busto, O.; Guasch, J. Analysis of organic sulfur compounds in wine aroma. J. Chromatogr., A 2000, 881, 569-581.
    • (2000) J. Chromatogr., A , vol.881 , pp. 569-581
    • Mestres, M.1    Busto, O.2    Guasch, J.3
  • 2
    • 0542441666 scopus 로고
    • Identification of new sulfur-containing volatiles in yellow passion fruits (Passiflora edulis f. flavicarpa)
    • Engel, K. H.; Tressl, R. Identification of new sulfur-containing volatiles in yellow passion fruits (Passiflora edulis f. flavicarpa). J. Agric. Food Chem. 1991, 39, 2249-2252.
    • (1991) J. Agric. Food Chem , vol.39 , pp. 2249-2252
    • Engel, K.H.1    Tressl, R.2
  • 3
    • 0002232745 scopus 로고
    • Enantiomeric distribution of the chiral sulfur-containing alcohols in yellow and purple passion fruits
    • Weber, B.; Maas, B.; Marz, A.; Olk, J.; Mosandl, A. Enantiomeric distribution of the chiral sulfur-containing alcohols in yellow and purple passion fruits. Z. Lebensm. Unters. Forsch. 1994, 199, 48-50.
    • (1994) Z. Lebensm. Unters. Forsch , vol.199 , pp. 48-50
    • Weber, B.1    Maas, B.2    Marz, A.3    Olk, J.4    Mosandl, A.5
  • 4
    • 0001323046 scopus 로고    scopus 로고
    • Vacuum headspace method in aroma research: Flavor chemistry of yellow passion fruits
    • Werkhoff, P.; Guntert, M.; Krammer, G.; Sommer, H.; Kaulen, J. Vacuum headspace method in aroma research: flavor chemistry of yellow passion fruits. J. Agric. Food Chem. 1998, 46, 1076-1093.
    • (1998) J. Agric. Food Chem , vol.46 , pp. 1076-1093
    • Werkhoff, P.1    Guntert, M.2    Krammer, G.3    Sommer, H.4    Kaulen, J.5
  • 5
    • 0031825535 scopus 로고    scopus 로고
    • Identification of new volatile thiols in the aroma of Vitis vinifera L. var. Sauvignon
    • Tominaga, T.; Furrer, A.; Henry, R.; Dubourdieu, D. Identification of new volatile thiols in the aroma of Vitis vinifera L. var. Sauvignon. Flavour Fragrance J. 1998, 13, 159-162.
    • (1998) Flavour Fragrance J , vol.13 , pp. 159-162
    • Tominaga, T.1    Furrer, A.2    Henry, R.3    Dubourdieu, D.4
  • 7
    • 0033999226 scopus 로고    scopus 로고
    • Identification of impact odorants in Bordeaux reg grape juice, in the commercial yeast used for its fermentation and in the produced wine
    • Kotseridis, Y.; Baumes, R. Identification of impact odorants in Bordeaux reg grape juice, in the commercial yeast used for its fermentation and in the produced wine. J. Agric. Food Chem. 2000, 48, 400-406.
    • (2000) J. Agric. Food Chem , vol.48 , pp. 400-406
    • Kotseridis, Y.1    Baumes, R.2
  • 8
    • 0000345542 scopus 로고
    • Stereoisomeric flavor compounds. 72. Stereoisomeric distribution of some chiral sulfur-containing trace components of yellow passion fruits
    • Weber, B.; Maas, B.; Mosandl, A. Stereoisomeric flavor compounds. 72. Stereoisomeric distribution of some chiral sulfur-containing trace components of yellow passion fruits. J. Agric. Food Chem. 1995, 43, 2438-2441.
    • (1995) J. Agric. Food Chem , vol.43 , pp. 2438-2441
    • Weber, B.1    Maas, B.2    Mosandl, A.3
  • 9
    • 0642378049 scopus 로고    scopus 로고
    • Identification of character impact odorants of different white wine varieties
    • Guth, H. Identification of character impact odorants of different white wine varieties. J. Agric. Food Chem. 1997, 45, 3022-3026.
    • (1997) J. Agric. Food Chem , vol.45 , pp. 3022-3026
    • Guth, H.1
  • 10
    • 0014208692 scopus 로고
    • Catty odors in food: Reactions between hydrogen sulfide and unsaturated ketones
    • Pearce, T. J. P.; Peacock, J. M.; Aylward, F.; Haisman, D. R. Catty odors in food: reactions between hydrogen sulfide and unsaturated ketones. Chem. Ind. 1967, 37, 1562-1563.
    • (1967) Chem. Ind , vol.37 , pp. 1562-1563
    • Pearce, T.J.P.1    Peacock, J.M.2    Aylward, F.3    Haisman, D.R.4
  • 11
    • 0029193852 scopus 로고
    • Identification of a powerful aromatic compound of Vitis vinifera L. var. Sauvignon wines: 4-mercapto-4-methylpentan-2-one
    • Darriet, P.; Tominaga, T.; Lavigne, V.; Boidron, J.; Dubourdieu, D. Identification of a powerful aromatic compound of Vitis vinifera L. var. Sauvignon wines: 4-mercapto-4-methylpentan-2-one. Flavour Fragrance J. 1995, 10, 385-392.
    • (1995) Flavour Fragrance J , vol.10 , pp. 385-392
    • Darriet, P.1    Tominaga, T.2    Lavigne, V.3    Boidron, J.4    Dubourdieu, D.5
  • 12
    • 0001389623 scopus 로고    scopus 로고
    • A new type of flavor precursor in Vitis vinifera L. cv. Sauvignon blanc: 5-cysteine conjugates
    • Tominaga, T.; Peyrot des Gachons, C.; Dubourdieu, D. A new type of flavor precursor in Vitis vinifera L. cv. Sauvignon blanc: 5-cysteine conjugates. J. Agric. Food Chem. 1998, 46, 5215-5219.
    • (1998) J. Agric. Food Chem , vol.46 , pp. 5215-5219
    • Tominaga, T.1    Peyrot des Gachons, C.2    Dubourdieu, D.3
  • 13
    • 0033929272 scopus 로고    scopus 로고
    • Identification of cysteinylated aroma precursors of certain volatile thiols in passion fruit juice
    • Tominaga, T.; Dubourdieu, D. Identification of cysteinylated aroma precursors of certain volatile thiols in passion fruit juice. J. Agric. Food Chem. 2000, 48, 2874-2876.
    • (2000) J. Agric. Food Chem , vol.48 , pp. 2874-2876
    • Tominaga, T.1    Dubourdieu, D.2
  • 14
    • 0033851483 scopus 로고    scopus 로고
    • Measuring the aromatic potential of Vitis vinifera L. cv. Sauvignon blanc grapes by assaying S-cysteine conjugates, precursors of the volatile thiols responsible for their varietal aroma
    • Peyrot des Gachons, C.; Tominaga, T.; Dubourdieu, D. Measuring the aromatic potential of Vitis vinifera L. cv. Sauvignon blanc grapes by assaying S-cysteine conjugates, precursors of the volatile thiols responsible for their varietal aroma. J. Agric. Food Chem. 2000, 48, 3387-3391.
    • (2000) J. Agric. Food Chem , vol.48 , pp. 3387-3391
    • Peyrot des Gachons, C.1    Tominaga, T.2    Dubourdieu, D.3
  • 15
    • 0037014370 scopus 로고    scopus 로고
    • Sulfur aroma precursor present in S-glutathione conjugate form: Identification of S-3-(hexan-1-ol)-glutathione in must from Vitis vinifera L. cv. Sauvignon Blanc
    • Peyrot des Gachons, C.; Tominaga, T.; Dubourdieu, D. Sulfur aroma precursor present in S-glutathione conjugate form: identification of S-3-(hexan-1-ol)-glutathione in must from Vitis vinifera L. cv. Sauvignon Blanc. J. Agric. Food Chem. 2002, 50, 4076-4079.
    • (2002) J. Agric. Food Chem , vol.50 , pp. 4076-4079
    • Peyrot des Gachons, C.1    Tominaga, T.2    Dubourdieu, D.3
  • 18
    • 0347355024 scopus 로고    scopus 로고
    • Stereochemical course of the generation of 3-mercaptohexanal and 3-mercaptohexanol by β-lyase-catalyzed cleavage of cysteine conjugates
    • Wakabayashi, H.; Wakabayashi, M.; Eisenreich, W.; Engel, K.-H. Stereochemical course of the generation of 3-mercaptohexanal and 3-mercaptohexanol by β-lyase-catalyzed cleavage of cysteine conjugates. J. Agric. Food Chem. 2004, 52, 110-116.
    • (2004) J. Agric. Food Chem , vol.52 , pp. 110-116
    • Wakabayashi, H.1    Wakabayashi, M.2    Eisenreich, W.3    Engel, K.-H.4
  • 20
    • 33645242517 scopus 로고    scopus 로고
    • Evidence for an alternative biogenetic pathway leading to 3-mercaptohexanol and 4-mercapto-4-methylpentan-2-one in wines
    • Schneider, R.; Charrier, F.; Razungles, A.; Baumes, R. Evidence for an alternative biogenetic pathway leading to 3-mercaptohexanol and 4-mercapto-4-methylpentan-2-one in wines. Anal. Chim. Acta 2006, 563, 58-64.
    • (2006) Anal. Chim. Acta , vol.563 , pp. 58-64
    • Schneider, R.1    Charrier, F.2    Razungles, A.3    Baumes, R.4
  • 21
    • 33749674486 scopus 로고    scopus 로고
    • Stereoisomeric distribution of 3-mercaptohexan-1-ol and 3-mercaptohexyl acetate in dry and sweet white wines made from Vitis vinifera (var. Sauvignon Blanc and Semillon)
    • Tominaga, T.; Niclass, Y.; Frérot, E.; Dubourdieu, D. Stereoisomeric distribution of 3-mercaptohexan-1-ol and 3-mercaptohexyl acetate in dry and sweet white wines made from Vitis vinifera (var. Sauvignon Blanc and Semillon). J. Agric. Food Chem. 2006, 54, 7251-7255.
    • (2006) J. Agric. Food Chem , vol.54 , pp. 7251-7255
    • Tominaga, T.1    Niclass, Y.2    Frérot, E.3    Dubourdieu, D.4
  • 23
    • 0034522070 scopus 로고    scopus 로고
    • Quantitative determination of sulfur-containing wine odorants at sub-ppb levels. 1. Synthesis of the deuterated analogues
    • Kotseridis, Y.; Baumes, R. Quantitative determination of sulfur-containing wine odorants at sub-ppb levels. 1. Synthesis of the deuterated analogues. J. Agric. Food Chem. 2000, 48, 5819-5823.
    • (2000) J. Agric. Food Chem , vol.48 , pp. 5819-5823
    • Kotseridis, Y.1    Baumes, R.2
  • 24
    • 84989478646 scopus 로고
    • Activated dimethyl sulfoxide: Useful reagents for synthesis
    • Mancuso, A. J.; Swern, D. Activated dimethyl sulfoxide: useful reagents for synthesis. Synthesis 1981, 165-185.
    • (1981) Synthesis , pp. 165-185
    • Mancuso, A.J.1    Swern, D.2
  • 25
    • 0035912338 scopus 로고    scopus 로고
    • New methods for side-chain protection of cysteine
    • West, C. W.; Estiarte, M. A.; Rich, D. H. New methods for side-chain protection of cysteine. Org. Lett. 2001, 3, 1205-1208.
    • (2001) Org. Lett , vol.3 , pp. 1205-1208
    • West, C.W.1    Estiarte, M.A.2    Rich, D.H.3
  • 26
    • 0242439381 scopus 로고    scopus 로고
    • Analysis of a model reaction system containing cysteine and (E)-2-methyl-2-butenal, (E)-2-hexenal, or mesityl oxide
    • Starkenmann, C. Analysis of a model reaction system containing cysteine and (E)-2-methyl-2-butenal, (E)-2-hexenal, or mesityl oxide. J. Agric. Food Chem. 2003, 51, 7146-7155.
    • (2003) J. Agric. Food Chem , vol.51 , pp. 7146-7155
    • Starkenmann, C.1
  • 27
    • 34547742001 scopus 로고    scopus 로고
    • Characterisation and simple synthesis of S-[3-hydroxy-1-propylpropyl]-L-cysteine
    • Luisier, J.-L.; Veyrand, J.; Piantini, U. Characterisation and simple synthesis of S-[3-hydroxy-1-propylpropyl]-L-cysteine. Chimia 2007, 61, 533-535
    • (2007) Chimia , vol.61 , pp. 533-535
    • Luisier, J.-L.1    Veyrand, J.2    Piantini, U.3
  • 28
    • 0000961325 scopus 로고
    • Synthesis of peptides containing S-(N-akylcarbamoyl) cysteine residues, metabolites of N-alkylformamides in rodents and in humans
    • Threadgill, M. D.; Gledhill, A. P. Synthesis of peptides containing S-(N-akylcarbamoyl) cysteine residues, metabolites of N-alkylformamides in rodents and in humans. J. Org. Chem. 1989, 54, 2940-2949.
    • (1989) J. Org. Chem , vol.54 , pp. 2940-2949
    • Threadgill, M.D.1    Gledhill, A.P.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.