Stereospecific synthesis of retinoic acid glucoconjugates, as pseudo- substrates of epidermal β-glucocerebrosidase

Tetrahedron Letters

Volumn 40, Issue 26, 1999, Pages 4811-4814

  Redoulès, Daniel ^a   Perié, Jacques ^b  

^a INSTITUT DE RECHERCHE PIERRE FABRE   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

GLUCOSYLCERAMIDASE; GLUCOSYLCERAMIDE; RETINOIC ACID DERIVATIVE; SKIN LIPID;

ARTICLE; DIASTEREOISOMER; DRUG CONJUGATION; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME SUBSTRATE COMPLEX; EPIDERMIS; LIPOGENESIS; SKIN DISEASE; STEREOSPECIFICITY;

EID: 0033603432     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00920-X     Document Type: Article

References (18)

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16. 3, 50 MHz) δ ppm : 167, 166.5 (C-15′, 15″), 154.3 (C-13′, 13″), 140 (C-9′, 9″), 137.7 (C-6,′ 6″), 137.3 (C-8, 8″), 135.1 (C-12′, 12″), 131.6 (C-11′, 11″), 130.4 (C-5′, 5″), 129.6 et 128.8 (C-10′, 10″, 7′, 7″), 117.9 (C-14′, 14″),103.7 (C-1), 76.1 (C-8), 73.7 (C-3,5), 70 (C-2,4), 68.3 (C-7), 62.5 (C-9), 62 (C-6), 39.6 (C-2′, 2″), 34.3 (C-1′, 1″), 33.2 (C-4′, 4″), 29 (C-16′, 16″, 17′, 17″), 21.8 (C-18′, 18″), 19.3 (C-3′, 3″), 13.8 et 13 (C-20′, 20″, 19′, 19″)
17. 3, 50 MHz) δ ppm : 167.2 (C-15′, 15″), 154.3 (C-13′, 13″), 140 ;1 (C-9′, 9″), 137.7 (C-6,′ 6″), 137.3 (C-8, 8″), 134.5 (C-12′, 12″), 131.6 (C-11′, 11″), 130.2 (C-5′, 5″), 129.5 et 129 (C-10′, 10″, 7′, 7″), 117.5 (C-14′, 14″), 68.7 (C-2), 64.8 (C-3), 62.2 (C-1), 39.6 (C-2′, 2″), 34.3 (C-1′, 1″), 33.2 (C-4′, 4″), 29 (C-16′, 16″, 17′, 17″), 21.8 (C-18′, 18″), 19.3 (C-3′, 3″), 14 et 13 (C-20′, 20″, 19′, 19″)
18. We thank Pr D. Fournier for providing the enzyme.