Determination of absolute stereochemistry of natural alicyclic glycosides by 1H NMR spectroscopy without application of chiral reagents - An indication

Natural Product Communications

Volumn 6, Issue 5, 2011, Pages 673-676

  Makariev, Tatyana N ^a   Shubina, Larisa K ^a   Guzii, Alla G ^a   Ivanchina, Natalya V ^a   Denisenko, Vladimir A ^a   Afiyatullov, Shamil S ^a   Dmitrenok, Pavel S ^a   Kalinovsky, Anatoly I ^a   Stonik, Valentin A ^a  

^a PACIFIC INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

Author keywords

Absolute stereochemistry; D and L sugars; Glycosides; NMR spectroscopy

Indexed keywords

AGLYCONE; ALPHA ARABINOPYRANOSIDE; ARABINOSE; BETA GLUCOPYRANOSIDE; GLUCOSE; GLYCOSIDE; LEVO GLUCOSE; MONOSACCHARIDE; OCTANOL; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; CONTROLLED STUDY; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

BIOLOGICAL PRODUCTS; GLYCOSIDES; MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM;

EID: 79955793184     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

1. (a) Dale JA, Dull DL, Mosher HS. (1969) α-Methoxy-α- trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines. Journal of Organic Chemistry, 34, 2543-2549;
2. (b) Dale JA, Mosher HS. (1973) Nuclear magnetic resonance enantiomeric reagents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate and α-methoxy- α-trifluoromethylphenylacetate (MTPA) esters. Journal of the American Chemical Society, 95, 512-519;
3. (c) Ohtani I, Kusumi T, Kashman Y, Kakisawa H. (1991) High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids. Journal of the American Chemical Society, 113, 4092-4096.
4. (a) Guzii AG, Makarieva TN, Denisenko VA, Dmitrenok PS, Kuzmich AS, Dyshlovoy SA, Krasokhin VB, Stonik VA. (2010) Monanchocidin: a new apoptosis -inducing polycyclic guanidin alkaloid from the marine sponge Monanchora pulchra. Organic Letters, 12, 4292-4295;
5. (b) Shubina LK, Makarieva TN, Dyshlovoy SA, Fedorov SA, Dmitrenok PS, Stonik VA. (2010) Three new aaptamines from the sponge Aaptos sp and their proapotic properties. Natural Product Communications, 5, 1881-1884.
6. Seo S, Tomita Y, Tori K, Yoshimura Y. (1978) Determinmation of the absolute configuration of chiral secondary alcohol using glycosylation shift in carbon-13 magnetic resonance spectroscopy. Journal of the American Chemical Society, 100, 3331-3337.
7. (a) Faghih R, Fontaine C, Horibe I., Imamura PM, Lukasc G, Olesker A, Seo S. (1985) Determination of the absolute configuration of chiral secondary alcohols from tetra-O-acetylglucosidation-induced H-1 nuclear magnetic resonance shifts. Journal of Organic Chemistry, 50, 4918-4920;
8. (b) Seroka P, Plosinski M, Czub J, Sowinski P, Pawlak J. (2006) Monosaccharides as internal probes for determination of the absolute configuration of 2-butanol. Magnetic Resonance in Chemistry, 44, 132-138;
9. 13C chemical shifts on the spatial interaction of protons, and its application in structural and conformational studies of oligo-saccharide and poly-saccharide. Carbohydrate Research, 133, 173-185;
10. 13C chemical shifts in carbohydrates. Magnetic Resonance in Chemistry, 26, 735-747;
11. (e) Lipkind GM, Shashkov AS, Mamyan SS, Kochetkov NK. (1988) The nuclear Overhauser effect and structural factors determining the conformations of disaccharide glycosides. Carbohydrate Research, 181, 1-12;
12. (f) Nicholas GM, Hong TW, Molinski TF, Lerch ML, Cancilla MT, Lebrilla CB. (1999) Oceanapiside, an antifungal bis-α,ω-amino alcohol glycoside from the marine sponge Oceanapia phillipensis. Journal of Natural Products, 62, 1678-1681;
13. (g) Ybarra MI, Popich S., Borkowsky SA, Asakawa Y, Bardon A. (2005) Manoyl oxide diterpenoids from Grindelia scorzonerifolia. Journal of Natural Products, 68, 554-558;
14. (h) Mayorga H, Duque C, Knapp H, Winterhalter P. (2002) Hydroxyester disaccharides from fruits of cape gooseberry (Physalis peruviana). Phytochemistry, 59, 439-445. (Pubitemid 34202564)
15. Minale L, Riccio R, Zollo F. (1993) Steroid oligoglycosides and polyhydroxysteroids from Echinoderms. In Progress in the Chemistry of Organic Natural Products. Herz H, Kirby GW, Moore RE, Steglich W, Tamm Ch. (Eds). Springer-Verlag, 62, 75-308.
16. (a) Stonik VA (2001) Marine polar steroids. Uspekhi khimii (Russian Chemical Reviews), 70, 673-715;
17. (b) Stonik VA, Ivanchina NV, Kicha AA. New polar steroids from starfish. Natural Product Communications, 3, 1587-1610;
18. (c) Ilyin SG, Reshetnyak MV, Schedrin AP, Struchkov JuT, Kapustina II, Stonik VA, Elyakov GB. (1990) Crystal and molecular structure of 6α,8β,15β-trihydroxy-3β,24R-di-(O-xylopyranosyl) -5α-cholest-22(23)-ene trihydrate. Doklady Akademii Nauk SSSR, 314, 637-639.
19. (a) Ivanchina NV, Kicha AA, Kalinovsky AI, Dmitrenok PS, Prokof'eva NG, Stonik VA. (2001) New steroid glycosides from the starfish Asterias rathbuni. Journal of Natural Products, 64, 945-947;
20. (b) Kicha AA, Kapustina II, Ivanchina NV, Kalinovsky AI, Dmitrenok PS, Stonik VA, Palyanova NV, Pankova TM, Starostina MV (2008) Polyhydroxylated steroid compounds from the Far-Eastern starfish Distolasterias nipon. Russian Journal of Biorganic Chemistry, 34, 118-124. (Pubitemid 351650951)