bluuebunny/crossref_metadata_2025_split huggingface dataset:
Secondary Metabolites by Chemical Screening, 23. Waraterpols, New Penicillium Metabolites and Their Derivatives
Authors: Henne Petra , Thiericke Ralf , Grabley Susanne , Hütter Klaus , Wink Joachim , Jurkiewicz Elke , Zeeck Axel 
Published: July 2007

AbstractSubstituted phenols can easily be recognized by using the chemical screening method, whereby they are found to be widely spread secondary metabolites of microorganisms. In the culture filtrate of Penicillium sp. (strain FH‐A 6260) new phenols named waraterpols were detected by a striking purple coloration by using anisaldehyde/sulfuric acid. These secondary metabolites (1 to 3 and 6 to 8) exhibit a C15‐carbon skeleton and can be characterized as hydroxylated branched‐chain sesquiterpenoids with a benzoide moiety. The minor compounds were O‐acetyl (2 and 3) and dehydrated derivatives (6 to 8) of the parent compound waraterpol (1), which was shown to be 6‐[2‐hydroxy‐4‐(hydroxymethyl)phenyl]‐2‐methylheptane‐1,6‐diol. Derivatization of 1 resulted in the quinone and hydroquinone compounds 10 and 5 as well as in the cyclic derivatives 11 and 12. The waraterpols exhibit distinct antibacterial and antifungal activities whereas an inhibition of HIV‐1 in a MT‐4 cell assay was found for 11.
Stereoselective synthesis of (2S,3S)‐norstatine derivatives by addition of lithiated methoxyallene to amino aldehydes and subsequent ozonolysis
Authors: Hormuth Stephan , Reißig Hans‐Ulrich , Dorsch Dieter 
Published: July 2007

AbstractAddition of lithiated methoxyallene 2 to optically active N‐benzyl‐Boc‐protected amino aldehydes 12–14 and to aldehyde 16 provides products 17–20 with good to excellent diastereoselectivity. These adducts are subsequently cleaved by ozonolysis to give α‐hydroxy‐β‐amino acid derivatives 21–25 in good overall yield. By conversion into an oxazolidone derivative, the configuration of the major diastereomer was determined to be anti (2S,3S). Thus, the additions of 2 follow the course proposed by the Felkin‐Anh model and are not ruled by chelation effects. The diastereoselective synthesis of 22 constitutes one of the simplest routes to a protected norstatine derivative. magnified image
Properties and reactions of substituted 1,2‐thiazetidine 1,1‐dioxides: Synthesis of 1,2‐thiazetidine‐2,3‐diacetic acid derivatives and their rearrangement to 1,2‐thiazinan‐3‐ones
Authors: Schwenkkraus Peter , Otto Hans‐Hartwig 
Published: July 2007

Abstractβ‐Sultam‐3‐acetic acid ester 3 prepared from rac‐S‐benzyl‐β‐homocysteine is alkylated with bromoacetates yielding diacetates 9 which are transformed into the phenylthio esters 11. The thiazinanone derivatives 12 are obtained from 11 by rearrangement with lithium bis(trimethylsilyl)amide in excellent yields, and the syntheses of the derivatives 13, 14, and 15 are described. The stereochemistry of all products is elucidated by spectroscopic methods, and a reaction pathway is proposed. It is supported by the synthesis of the isomeric β‐sultam‐2,3‐diacetate 20, which does not rearrange to a thiazinanone derivative. Some side reactions are described. magnified image
Antibiotics from gliding bacteria, LVII. Tartrolons: New boron‐containing macrodiolides from Sorangium cellulosum
Authors: Schummer Dietmar , Irschik Herbert , Reichenbach Hans , Höfle Gerhard 
Published: July 2007

AbstractThe antibacterial metabolites tartrolon A1, A2, A3 (1a–1c) and B (2) were isolated from the myxobacterium Sorangium cellulosum, strain So ce678. Large‐scale production was achieved by fermentation in the presence of the adsorber resin XAD‐16, extraction, and separation by RP chromatography followed by crystallization. The 42‐membered macrodiolide structure of 1a–1c and 2 was determined by spectroscopic methods. Compound 2 was identified as a boric acid ester of 1c, whereas 1a and 1b are stereoisomers of 1c. All components could be chemically converted into each other. A correlation between the production of 2 and the borate concentration in the medium was found, depending on nutrients and container material used. magnified image
The chemistry of unusual macrolides, 2. Spectroscopic and biosynthetic investigations of the V‐type ATPase inhibitor concanamycin A
Authors: Bindseil Kai U. , Zeeck Axel 
Published: July 2007

AbstractThe 1H‐ and 13C‐NMR spectra of the conformationally flexible macrolide concanamycin A (1) have been assigned by the use of 2D NMR techniques at low temperatures and have enabled biosynthetic studies on this most potent inhibitor of vacuolar ATPases. By feeding of different [13C]‐labeled precursors to Streptomyces sp. (strain Gö 22/15) the polyketide origin of the concanamycin skeleton was proved. It arises from a tetradecaketide, which is based on four acetate and seven propionate units besides one butyrate and two unusual C2 building blocks from the triose pool. In combination with former findings it is possible to predict the biogenetic assembly of several strongly related unusual macrolides, for which the group name “plecomacrolides” should be used in future. The results are discussed in the light of modern hypothesis as stated for polyketide pathways. magnified image
Synthesis of New Terpene Skeletons by Chemical Cyclization of Epoxy Olefins
Authors: Mori Kenji , Aki Shinji , Kido Masaru 
Published: July 2007

AbstractTin(IV) chloride catalyzed cyclization of the epoxy olefin (±)‐7 gave the octahydroazulene derivative (±)‐9, the structure of which was solved by X‐ray analysis of its derivative (±)‐11. Titanium(IV) chloride catalyzed cyclization of the epoxy triene (±)‐18 yielded the hydrobenz[e]indene derivative (±)‐19 as a mixture of stereoisomers. The structure of (±)‐19 was solved by X‐ray analyses of its derivatives (±)‐20 and (±)‐21. magnified image
Structure‐Odor Correlation, XIX. Synthesis and Olfactory Properties of Various Racemic Theaspirones, Ketoedulans and Edulans
Authors: Weyerstahl Peter , Meisel Thomas 
Published: July 2007

AbstractStarting from the cheap isophorone derivative 1 and the alkynols 2–4, we could prepare the key intermediates 9–11 via addition reaction (→ 5–7) and hydrogenation. Ring closure of 9–11 led to the theaspirone (C) and/or ketoedulan (E) series, depending on the reaction conditions used and the steric situation at C‐2. By treatment of 9 with tosyl chloride/pyridine the theaspirone derivative 13 was formed exclusively, whereas 10a, b were converted into mixtures of 14a, b together with the ketoedulan derivatives 20a, b; the crowded 11 did not react at all. By treatment of 9–11 with hydrochloric acid/acetone 19–21 were readily obtained. Several hydrogenation and dehydration steps under various conditions led to the theaspirones 16–18, to the ketoedulans 26a, b and 27, and to the edulans 39a and 40b. – Olfactory evaluation of the theaspirones 16 (harsh, green), 17a (floral, fruity) and 18 (weak, woody) shows the drastic influence of the steric situation at C‐2. The ketoedulans 26a and 27 smell weak, woody. Evaluation of both odor and flavor of 39a and 40b exhibits mostly woody, camphoraceous and fruity tonalities. magnified image
Semicyclic 3‐Trifloxypropen‐ and Propyniminium Triflates
Authors: Reinhard Robert , Maas Gerhard , Bohrisch Jörg , Liebscher Jürgen 
Published: July 2007

AbstractO‐Sulfonylation of 2‐oxomethylene‐substituted 1‐azaheterocycles 1 yields the 3‐trifloxypropeniminium triflates 2a–e in high yield. Thermal β‐elimination of triflic acid from these salts affords the propyniminium triflates (2‐ethynylcycliminium triflates) 3a–e. The treatment of semicyclic enamino ketones 1f, g with triflic anhydride yields directly the propyniminium triflates 3f, g. magnified image
Die Oxidation zweier neuer 1,3‐Dihydroxyimidazolidine – Darstellung und Struktur von Nitronylnitroxid‐Radikalen
Authors: Bätz Christof , Amann Peter , Deiseroth Hans‐Jörg , Dulog Lothar 
Published: July 2007

The Oxidation of Two New 1,3‐Dihydroxyimidazolidines – Synthesis and Structure of Nitronyl Nitroxide RadicalsThe two new 1,3‐dihydroxyimidazolidines 3a and 3b were prepared by condensation of 4‐formylbenzoic acid (2a) and sodium glyoxylate (2b) with 2,3‐dimethyl‐2,3‐butanediylbis‐(hydroxylamine) sulfate (1). The 1,3‐dihydroxyimidazolidines were oxidized with sodium periodate in water to form nitronyl nitroxide radicals. Oxidation of the 1,3‐dihydroxyimidazolidine 3a yielded the new radical 4a, whereas the product obtained from the 1,3‐dihydroxyimidazolidine 3b was, due to decarboxylation, the unsubstituted radical 4c. The crystal structure of 4a was solved by single‐crystal X‐ray diffraction, showing the molecules to be arranged in zigzag chains as a consequence of intermolecular hydrogen bonds. magnified image
Aborycin – A Tricyclic 21‐Peptide Antibiotic Isolated from Streptomyces griseoflavus
Authors: Potterat Olivier , Stephan Holger , Metzger Jörg W. , Gnau Volker , Zähner Hans , Jung Günther 
Published: July 2007

AbstractThe screening for growth inhibitors against Bacillus subtilis revealed a peptide antibiotic produced by Streptomyces griseoflavus TÜ 4072. Very high yields of the antibiotic named aborycin were obtained by cultivation in a medium containing soybean meal and sucrose. Isolation from the mycelium was carried out by a combination of extraction and gel chromatography. Preparative HPLC yielded the uniform antibiotic. The structure elucidation was based on GC amino acid analysis on a chiral phase, automated Edman degradation, electrospray tandem mass spectrometry and two‐dimensional NMR (TOCSY, ROESY, HSQC, HMBC). Aborycin represents a 21‐peptide that is cyclized from the side chain of Asp9 to the N‐terminus of Cys1. Two disulfide bonds Cys1 to Cys13 and Cys7 to Cys19 form a tricyclic structure consisting exclusively of protein amino acids. The peptide antibiotic aborycin was found to be identical with a HIV protease inhibitor isolated recently from Streptomyces SP 9440. magnified image
Dimethyldioxirane Oxidation of 3‐Arylidenechromanones
Authors: Adam Waldemar , Halász Judit , Lévai Albert , Nemes Csaba , Patonay Tamás , Tóth Gábor 
Published: July 2007

AbstractOxidation of the (E) and (Z) isomers of the 3‐arylidenechromanones 5 by isolated dimethyldioxirane (as acetone solution) at ambient temperature resulted in the formation of the spiro epoxides trans‐ and cis‐6, respectively, in moderate yields (23–51%), together with considerable amounts (16–40%) of the 3‐aroylchromones 7 from both (E)‐ and (Z)‐5 isomers. Minor products, namely 3‐(α‐hydroxy‐4‐methoxy‐benzyl)‐4H‐1‐benzopyran‐4‐one (8b), 1a,7a‐dihydro‐7a‐(α‐hydroxy‐4‐methylbenzyl)‐7H‐oxireno[b][1]benzopyran‐7‐one (9d), and the 1a,7a‐dihydro‐7a‐aroyl‐7H‐oxireno[b][1]‐benzopyran‐4‐ones 10a–c have also been isolated and characterized. Presumably, the formation of 3‐aroylchromones 7 can be attributed to competitive allylic oxidation with dimethyldioxirane to afford first the 3‐(α‐hydroxyarylmethyl)‐chromones 8, whose secondary alcohol functionality is subsequently oxidized by dimethyldioxirane to give the 3‐aroylchromones 7. Further oxidation of the latter by dioxirane affords the epoxides 10, as established by a control experiment. Alternatively, first oxidation of 8 to yield epoxide 9 and subsequent oxidation of the alcohol functionality to afford the overoxidized product 10 cannot be disposed of on grounds of our product data. Nonetheless, despite the moderate yields of the desirable chromanone epoxides 6, the stereoselective oxidation directly of the chromanones by dimethyldioxirane offers a convenient preparation. Relative configuration and stereochemistry of compounds 6–10 were elucidated by NMR spectroscopy and AM1 calculations. magnified image
Synthese vonN‐substituierten Oxo‐ und Thioxopyrimidinen aus 1,2,4‐Dithiazoliumsalzen
Authors: Holzer Max , Dobner Bodo , Briel Detlef 
Published: July 2007

Synthesis ofN‐Substituted Oxo‐ and Thioxopyrimidines from 1,2,4‐Dithiazolium Salts2,4‐Diaryl‐substituted 1,3‐thiazine‐5‐carbonitriles5, 6, obtained by reaction of 1,2,4‐dithiazolium salts1with activated cyanoacetates, undergo ring transformations in the presence of primary and secondary amines. Thus,5and6react with primary amines under mild conditions to give hardly accessible N‐3‐substituted oxopyrimidine‐ or thioxopyrimidine‐5‐carbonitriles11, 16, with secondary amines to give N‐3‐unsubstituted pyrimidine derivates14, 19and with diamines to give imidazo[1,2‐c]pyrimidines or pyrimido[1,2‐c]pyrimidines23a, b. After alkylation of 1,3‐thiazines6, highly reactive 1,3‐thiazinium salts8can be isolated.
Stereoselective Amidoalkylation Reactions via N,O‐Acetals
Authors: Arenz Thomas , Frauenrath Herbert , Raabe Gerhard , Zorn Martin 
Published: July 2007

AbstractThe isomerization of N,O‐acetals 1 yields N‐acyl‐O‐vinyl acetals 2 or 2‐aminomethyl‐1,3‐butadienes 10, depending on the nature of the nitrogen substituents. In the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) the N,O‐acetals 2h–u are converted stereoselectively into β‐(N‐acylamino)aldehydes 3. The relative configurations of the products 3 have been determined by X‐ray analysis and 1H‐NMR experiments. The mechanism of the reaction is discussed. Crossover experiments indicate an intermolecular course of the rearrangement.
Derivate der Ketipinsäure, II. Ketipinsäuredilacton und verwandte Verbindungen
Authors: Stachel Hans‐Dietrich , Jungkenn Michael , Koser‐Gnoss Christiane , Poschenrieder Hermann , Redlin Jutta 
Published: July 2007

Derivatives of Ketipic Acid, II. – Ketipic Acid Dilactone and Related CompoundsThe highly reactive title compound 7 was prepared by thermal decomposition of the disguised oxalylbisketene 6. Ring opening of 7 with nucleophiles leads to γ‐alkylidenetetronic acids 4. α‐Substituted derivatives of 4a give rise to unsymmetrical dilactones 9a–c and the dibromodilactone 9d. The alkylidenetetronic acids are stabilized in the E configuration by hydrogen bridges. The pairs of isomeric (E)‐ and (Z)‐alkylidenetetronic acids 3 and 4 show characteristic spectral differences.
Synthesis of Carbon‐Bridged C‐Lactose and Derivatives
Authors: Dietrich Hansjörg , Schmidt Richard R. 
Published: July 2007

Abstract4‐C‐Formylglucopyranoside 9 was readily obtained from 4‐O‐unprotected glucose derivative 4 in four steps, each step giving a high product yield. Reaction with 1‐C‐lithiated 2‐phenylsulfinyl‐D‐galactal 10 as nucleophile furnished C‐disaccharide intermediates 11a and 11b as diastereoisomers. Ensuing removal of the phenylsulfinyl group with Raney nickel and regio‐ and diastereospecific 2b‐hydrogen and 3b‐hydroxy transfer afforded β(1–4)‐connected C‐lactosides 13a and 13b, respectively; their structures were deduced from derivatives 14a, b and 16a, b on the basis of 1H‐NMR data. Hydrogenolytic O‐debenzylation of 13a and 13b afforded hydroxymethylene‐bridged C‐lactose 2a and 2b, respectively. Regioselective O‐benzylation of 13a gave preferentially 1b‐O‐unprotected derivative 17aa which furnished upon oxidation carbonyl‐bridged C‐lactose derivative 19. Deoxygenation at C‐1b of 17aa and subsequent hydrogenolytic O‐debenzylation furnished methylene‐bridged C‐lactose 1.
Synthesen von 20‐Carbaldehyden und 20‐Carbonitrilen der Pregnanreihe aus (20S)‐20‐Hydroxymethylpregna‐1,4‐dien‐3‐on
Authors: Krieg Reimar , Schönecker Bruno 
Published: July 2007

Synthesis of 20‐Carbaldehydes and 20‐Carbonitriles of the Pregnane Series Starting with (20S)‐20‐Hydroxymethylpregna‐1,4‐dien‐3‐oneAn efficient six‐step approach to 3‐protected (20S)‐3β‐hydroxypregna‐1,5‐diene‐20‐carbaldehydes8with potential importance in the synthesis of vitamin D analogues was developed starting with (20S)‐20‐hydroxymethylpregna‐1,4‐dien‐3‐one (1). Oxidation of the 22‐hydroxy group of1by means of periodinane2(Dess‐Martin reagent) furnished the aldehyde3without epimerization.3was protected selectively at C‐22 as dimethyl acetal5. Isomerization to6and subsequent reduction of the 3‐carbonyl group with calcium borohydride furnished the 3β‐alcohol7awith high stereoselectivity. Cleavage of the acetal to8aoccurred in a homogeneous solution of acetic acid in the presence of small amounts of water and trifluoroacetic acid. After protection of the 3‐OH group8b–dwere obtained in 54% overall yield. The in situ generated aldehydeN,N‐dimethylhydrazones of3, 8a, and8bwere converted in high yields with excellent chemoselectivity into the nitriles12, 15a, and15bwith magnesium monoperoxyphthalate hexahydrate. The uniform (20S) stereochemistry of3and8a–dwas elucidated by1H‐NMR investigations.
A Short Synthesis of Vicine and Convicine, the Causative Agents of Favism
Authors: Kunesch Nicole , Miet Christine , Poisson Jacques 
Published: July 2007

AbstractVicine (1) and convicine (2) (Vicia faba), causative of the human disease favism, have been conveniently prepared in good yields by a three‐step synthesis starting from ethyl glyoxylate. The key step is the reaction of a suitable tetra‐O‐acetylglucopyranoside with a large excess of guanidine with causes simultaneously deacetylation and coupling.
Biologically Active Metabolites from Fungi, 4. Palmarumycins CP1–CP4 from Coniothyrium palmarum: Isolation, Structure Elucidation, and Biological Activity
Authors: Krohn Karsten , Michel Andreas , Flörke Ulrich , Aust Hans‐Jürgen , Draeger Siegfried , Schulz Barbara 
Published: July 2007

AbstractFour new penta‐ and hexacyclic antifungal and antibacterial metabolites, the palmarumycins CP1–CP4 (1–4), were isolated from Coniothyrium palmarum. In these structurally unique antibiotics, a 1,8‐dihydroxynaphthalene unit is connected by a spiroacetal to another partially reduced naphthalene unit. The structure of the pentacyclic palmarumycin CP3 (3) was confirmed by X‐ray structure analysis.
Synthesis of 13‐O‐β‐D‐Glucopyranosylgibberellin A5 β‐D‐Glucopyranosyl Ester
Authors: Schneider Gernot , Schmidt Jürgen 
Published: July 2007

Abstract13‐O‐β‐D‐Glucopyranosylgibberellin A5 β‐D‐glucopyranosyl ester (2a) was synthesized by base‐catalyzed (triethylamine) reaction of gibberellin A5 13‐O‐β‐D‐glucopyranoside (4a) with α‐acetobromoglucose followed by mild sodium methanolate deacetylation. Structures of the gibberellin A5 glucosyl conjugates were established by LSI‐MS, ESI‐MS, and 1H‐NMR spectroscopy.
Syntheses and Reactions of Crown Ether‐Bridged Stilbenes
Authors: Merz Andreas , Karl Andreas , Futterer Thomas , Stacherdinger Natascha , Schneider Oliver , Lex Johann , Luboch Elzbieta , Biernat Jan F. 
Published: July 2007

AbstractA high‐yield synthesis of o, o′ crown ether‐bridged stilbenes 3b–e by reductive McMurry condensation of (2‐formylphenyl)oligoethylene glycols 2b–e with facile (E/Z) diastereomer separation by selective cation complexation is described. Derivatization of the stilbene double bonds of (E)‐ or (Z)‐3b–e affords dihydroxy crown ethers 4c, d and 5c, d diastereo‐ and enantioselectively. Likewise, trans‐ and cis‐epoxides 11b–d and 12b–d are stereospecifically obtained. A crown ether‐bridged diphenylacetaldehyde 13 is formed by rearrangement of 11c or 12c. Photocyclization of 3e yields large‐ring 1,8‐phenanthrene crown ether 18. The crystal structures of racemic 5c and of 12d are presented. A high caesium selectivity compared to the other alkali metal and alkaline earth cations is found for ion exchange membranes with incorporated crown ether (Z)‐3c.
Nitro Ketones in Organic Synthesis: A New, Short Synthesis of Racemic trans‐2‐methyl‐1,7‐dioxaspiro[5.5]undecane, trans, trans‐ and trans, cis‐2,8‐dimethyl‐1,7‐dioxaspiro[5.5]undecane by Henry reaction
Authors: Ballini Roberto , Bosica Giovanna , Schaafstra Robert 
Published: July 2007

AbstractThe synthesis of spiroketals from nitro ketones is described. Racemic trans‐2‐Methyl‐1,7‐dioxaspiro[5.5]undecane (1a), and 2,8‐dimethyl‐1,7‐dioxaspiro[5.5]undecane (1b) are synthesized as a mixture of trans, trans and trans, cis isomers in a ratio of 6.5:3.5 (separable by flash chromatography) by nitroaldol reaction (Henry reaction) of 6‐nitro‐2‐hexanone (2) with THP‐protected hydroxy aldehydes 3 on Amberlyst A21. Subsequent dehydration of the obtained nitro alkanols 4 with Ac2O/DMAP affords the nitro alkenes 5 which can be directly converted into 1 by sodium tetrahydridoborate reduction, and refluxing of the reaction mixture after acidification with 2 N HCl.
The intestine as a possible target for fumonisin toxicity
Authors: Bouhet Sandrine , Oswald Isabelle P. 
Published: July 2007

AbstractFumonisins constitute a family of toxic and carcinogenic mycotoxins produced by Fusarium verticillioides (formerly F. moniliforme), a common fungal contaminant of corn. Contamination with fumonisin B1 (FB1) is of concern as this mycotoxin causes various animal diseases. The gastrointestinal tract represents the first barrier against ingested chemicals, food contaminants, and natural toxins. Following ingestion of fumonisin‐contaminated food or feed, intestinal epithelial cells could be exposed to a high concentration of toxin. In this review, we have summarized the data dealing with the impact of FB1 on the intestine. Although FB1 is poorly absorbed and metabolized in the intestine, it induces intestinal disturbances (abdominal pain or diarrhea) and causes extra‐intestinal organ pathologies (pulmonary edema, leukoencephalomalacia, or neural tube defects). The main toxicological effect of FB1 reported in vivo and in vitro is the accumulation of sphingoid bases associated with the depletion of complex sphingolipids. This disturbance of the sphingolipid biosynthesis pathway could explain the other observed toxicological effects such as an alteration in intestinal epithelial cell viability and proliferation, a modification of cytokine production, and a modulation of intestinal physical barrier function.
Characterization of antioxidant compounds of red and white rice and changes in total antioxidant capacity during processing
Authors: Finocchiaro Franca , Ferrari Barbara , Gianinetti Alberto , Dall'Asta Chiara , Galaverna Gianni , Scazzina Francesca , Pellegrini Nicoletta 
Published: July 2007

AbstractAlthough most rice cultivars have whitish kernel, some varieties have a red testa. Aim of this work was to compare the total antioxidant capacity (TAC) and the antioxidant chemical composition (namely tocols, γ‐oryzanols, and polyphenols) of red and white rices. In addition, the effect of milling and cooking on antioxidants was investigated in both rices. Dehulled red rice showed a TAC more than three times greater than dehulled white rice and its high TAC was essentially characterized by the presence of proanthocyanidins (PA) and associated phenolics. Milling caused a significant loss of TAC, even if red rice maintained a higher TAC. Cooking caused a further loss of antioxidants, but when there was a full uptake of cooking water by the grains (“risotto”) this loss was limited. Thus, the consumption of whole or partially milled rice cooked as risotto would be preferred to preserve its nutritional properties.
Complete 1H and 13C NMR spectral assignment of α‐ and β‐adenosine, 2′‐deoxyadenosine and their acetate derivatives
Authors: Ciuffreda P. , Casati S. , Manzocchi A. 
Published: July 2007

Abstract1H and 13C NMR chemical shifts of α‐ and β‐anomers of adenosine, 2′‐deoxyadenosine and their acetate derivatives were completely and definitely assigned using the concerted application of one‐ and two‐dimensional experiments (gCOSY, gNOESY, gHSQC and gHMBC). The influence of the stereochemistry of the purine base on the NMR data of the hydrogen and carbon atoms of the furanose moiety was estimated. Copyright © 2007 John Wiley & Sons, Ltd.
Determination of the anomeric configuration in carbohydrates by longitudinal cross‐correlated relaxation studies: application to mono‐ and disaccharides
Authors: Pichumani Kumar , Zou Xiang , Chandra Tilak , Brown Kenneth L. 
Published: July 2007

AbstractThe role of cross‐correlated relaxation between the anomeric proton chemical shift anisotropy (CSA) and its dipolar relaxation with nearby proton on the longitudinal relaxation in mono‐ and disaccharides at two magnetic field strengths has been investigated and shown to directly report the identity of their anomeric configuration. Copyright © 2007 John Wiley & Sons, Ltd.