Carbohydrate Chemistry
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Carbohydrate Chemistry provides review coverage of all publications relevant to the chemistry of monosaccharides and oligosaccharides in a given year.InhaltsverzeichnisIntroduction and general aspects free sugars glycosides and dis.
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- Title
- Carbohydrate Chemistry
- Author
- Ferrier, R. J.
- Publisher
- Royal Society of Chemistry
- Publication year
- 1990
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- Gebunden
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- English
- ISBN 10
- 0851862128
- ISBN 13
- 9780851862125
Carbohydrate Chemistry provides review coverage of all publications relevant to the chemistry of monosaccharides and oligosaccharides in a given year. The amount of research in this field appearing in the organic chemical literature is increasing because of the enhanced importance of the subject, especially in areas of medicinal chemistry and biology. In no part of the field is this more apparent than in the synthesis of oligosaccharides required by scientists working in glycobiology. Clycomedicinal chemistry and its reliance on carbohydrate synthesis is now very well established, for example, by the preparation of specific carbohydrate- based antigens, especially cancer-specific oligosaccharides and glycoconjugates. Coverage of topics such as nucleosides, amino-sugars, alditols and cyclitols also covers much research of relevance to biological and medicinal chemistry. Each volume of the series brings together references to all published work in given areas of the subject and serves as a comprehensive database for the active research chemist Specialist Periodical Reports provide systematic and detailed review coverage in major areas of chemical research. Compiled by teams of leading authorities in the relevant subject areas, the series creates a unique service for the active research chemist, with regular, in-depth accounts of progress in particular fields of chemistry. Subject coverage within different volumes of a given title is similar and publication is on an annual or biennial basis.
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Carbohydrate Chemistry Volume 22
Monosaccharides, Disaccharides, and Specific Oligosaccharides
By R. J. FerrierThe Royal Society of Chemistry
All rights reserved.
Contents
Chapter 1 Introduction and General Aspects, 1,
Chapter 2 Free Sugars, 3,
Chapter 3 Glycosides and Disaccharides, 15,
Chapter 4 Oligosaccharides, 46,
Chapter 5 Ethers and Anhydro-sugars, 56,
Chapter 6 Acetal, 65,
Chapter 7 Esters, 71,
Chapter 8 Halogeno-sugars, 86,
Chapter 9 Amino-sugars, 91,
Chapter 10 Miscellaneous Nitrogen Derivatives, 108,
Chapter 11 Thio-and Seleno-sugars, 120,
Chapter 12 Deoxy-sugars, 126,
Chapter 13 Unsaturated Derivatives, 136,
Chapter 14 Branched-chain Sugars, 145,
Chapter 15 Aldosuloses, Dialdoses, and Diuloses, 156,
Chapter 16 Sugar Acids and Lactones, 159,
Chapter 17 Inorganic Derivatives, 170,
Chapter 18 Alditols and Cyclitols, 177,
Chapter 19 Antibiotics, 192,
Chapter 20 Nucleosides, 205,
Chapter 21 N.M.R. Spectroscopy and Conformational Features, 228,
Chapter 22 Other Physical Methods, 237,
Chapter 23 Separatory and Analytical Methods, 248,
Chapter 24 Synthesis of Enantiomerically Pure Noncarbohydrate Compounds, 258,
Author Index, 271,
CHAPTER 1
Introduction and General Aspects
The field continues to develop on all fronts, and improvements in synthetic methodology are giving access to substantially more complex products. Nowhere is this move apparent than in oligosaccharide and C-glycoside synthesis and in the use of synthetic procedures which are dependent on carbohydrate-derived carbanions and particularly free radicals. The increasing interest shown by "non-carbohydrate chemists" in carbohydrate chemistry is welcomed; their contributions have enlivened the field appreciably as is best illustrated by their descriptions of novel approaches to glycoside synthesis and, of course, many syntheses of enantiomerically pure non-carbohydrates from sugars.
El Khadem has published a book "Carbohydrate Chemistry: Monosaccharides and their Oligomers", and reviews of general interest have appeared on the chemistry and biochemistry of the sweetness of sugars and on the use of immobilised enzymes in preparative carbohydrate chemistry.
Volume 45 of Advances in Carbohydrate Chemistry and Biochemistry (1987) contains articles on circular dichroism n.m.r. (proton relaxation rate data in structural analysis) and mass spectrometry (FAB methodology). The volume also contains tributes to the lives and work of Professors B. Helferich and F. C. Gonzalez.
The succeeding volume of the series contains reviews on H.p.l.c. of carbohydrates, n.m.r. of fluorinated monosaccharides," the use of photosensitive protecting groups in carbohydrate synthesis'' and high-temperature transformations of monosaccharides in aqueous solution.
Appreciations of the lives and work of Professor K. Onedera and V. Deulofeu are also included in this volume.
CHAPTER 2Free Sugars
1 Theoretical Aspects
Recent progress in the physical chemistry of small carbohydrate compounds has been reviewed. There is accumulating evidence that solvation plays an important part in determining the solution equilibria and conformational properties of sugars. The standard geometries of both anomers of the eight hexopyranoses in the 4C1 conformation have been calculated and are given in the form of orthogonal co-ordinates. The geometries found for pyranose rings corresponded to the averaged ring structures determined from X-ray diffraction analyses of 161 compounds (see B. Sheldrick and D. Akrigg, Acta Crystallogr., 1980, 836. 1615). A revised CHARMM molecular mechanics potential-energy function has been developed for use in the dynamical simulation of simple carbohydrates in aqueous solution. Application to the molecular dynamics simulation of the motions of α-D-glucopyranose in vacuo in both the 4C1 and 1C4 conformation produced a D-glucose molecule less flexible then had previously been determined. CNDO Force constants for both anomers of D-glucopyranose have been evaluated, and an ab initio investigation of the electronic structure of the α-D-glucose molecule by use of the Hartree-Fock-Roothan method has been carried out. The effective charges agreed with those derived from semi-empirical calculations.
The hydrophobic indices, i.e, the ratios of hydrophobic to hydrophilic surface areas, of seven monosaccharides have been determined. They were found to correlate well with the partition coefficients of the polystyrene-water system for monosaccharides. The concept of hydrophobic indices is important in the consideration of the hydrophobic interactions of flat molecules in aqueous solution. In an effort to establish quantitative structure-activity relationships for carbohydrates, an experimental data-matrix containing the Rf values of sixteen monosaccharides in thirteen solvent systems was subjected to principal component analysis (PCA). Four PC's (t1-t4) were found to explain 97.8% of the variance, and the first of these (t1), which described 90% of the variance, was tentatively interpreted as a hydrophobicity scale. Ab initio Calculations have shown that D-ribose is energetically stabilised relative to its L-enantiomer by parity-violating weak interaction (see Vol. 20, p. 2, ref. 4). The possible significance of these findings with regard to evolution has been pointed out.
2 Synthesis
A review on the synthesis of complex carbohydrates by a combination of chemical and enzymic methods has been published. A new strategy for the predictable creation of new chiral centres and its application to the synthesis of sugars and macrocycles is presented in a review on the use of double asymmetric induction in the aldol condensation, the Diels Alder cycloaddition, epoxidation and hydrogenation. Two approaches to the construction of appropriately functionalised six-carbon chains are outlined in a review on the dg novo synthesis of carbohydrates from achiral precursors: (i), hetero-Diels Alder reaction with inverse electron demand of functionalised 1-oxa-1, 3-dienes with dienophiles such as enol ethers followed by diastereoselective addition to the new double bond and (ii), Sharpless oxidation of racemic or meso-divinyl glycols, with concomitant kinetic resolution.
Sugars with four, six, and eight carbon atoms were formed from glycolaldehyde in an aqueous suspension of sodium montmorilIonite at 40°C, hexoses being the main products (see Vol. 20, p. 3, ref. 8). The conversion efficiency was 90% and an aldol-type mechanism has been suggested for the reaction. Aldoses are smoothly decarbonylated by chlorotris(triphenyl)rhodium in N-methylpyrrolidin-2-one at 130°C to give the next lower alditols. D-Glucose for example gives D-arabinose and 2-deoxv-D-erYthro-pentose gives 1-deoxyerythritol in 90% yield. Ketoses undergo more complex dehydration-decarbonylation reactions; thus furfuraldehyde was formed in 79% yield from fructose. Experiments with [1-13C]-labelled substrate showed that C-1 was lost during the reaction.
2.1 Pentoses. – On reaction with aqueous Pb(OH)2 3,4-Q-isopropylidene-L-arabinose rearranged to 2-deoxy-L-ribono-1, 4-lactone which was reduced to 2-deoxy-L-erythro-pentofuranose by sodium borohydride. 2,4-Q-Benzylidene-L-xylose has been prepared in high yield by periodate oxidation of 2,4-O-benzylidene-D-glucitol. Iron(III)trifluoroacetate proved to be an efficient catalyst in the preparation of D-[U-14C] arabinose and D-[U-14C] lyxose by Ruff degradation of universally labelled D-glucose and D-galactose, respectively. A new total synthesis of D- or L-ribose derivatives starts from the optically pure, functionalised oxabicycloheptene (1) (esterified with (-) camphanoic acid) or its enantiomer, respectively. The seven step reaction sequence leading to the D-product (2) is shown in Scheme 1.
2.2 Hexoses. – Strontium and calcium chloride have a marked effect on the selectivity of the triose aldose condensation. Under ordinary conditions, i.e.. in the absence of alkaline-earth metal ions, 3.4-threo configurated products, particularly arabino-2-hexulose (fructose) and xylo-2-hexulose(sorbose), prevail. Typically, the product composition is arabino : xylo : ribo : lyxo = 51 : 38 : 7 : 4. This diastereoselectivity is in accordance with a pericyclic reaction mechanism and the intermediacy of the transition state (3). In the presence of high concentrations of Sr2+ or Ca2+, increased proportions of hexuloses with the 3,4-erythro-configuration, especially the lyxo isomer, are formed at the expense of fructose (e.g.. arabino : xylo : ribo : lyxo = 22 : 34 : 12 : 32) indicating α-chelation and attack of the complex (4) by the dihydroxyacetone enolate from the least hindered side.
Derivatives (6) and (8) of D-psicofuranose and 1-deoxy-D-psicofuranose, respectively, have been synthesised by new routes from the protected D-ribonolactone derivative (5) as outlined in Scheme 2. Attempts to hydrolyse the dithiane (7) to an aldehyde were unsuccessful.
A simpler and more efficient version of the traditional Kiliani method has been used to prepare [6-13C] -labelled hexoses. K13CN was added to 1.2-O-isopropylidene-α-D-xvlo-pentodialdo-1.4-furanose. Hydrogenation of the adducts and in situ borohydride reduction followed by deprotection gave D-[6-13C]glucose and L-[6-13C]idose, which were separable on a DOWEX 50 x 8 (Ca2+) column. Molybdate epimerisation of these products afforded D-[6-13C]mannose and L-[6-13C]gulose. Procedures suitable for the large scale (50 g) production of 13C-enriched hexoses have been developed. D-[1-13C] glucose and D-[1-13C]mannose were prepared from D-arabinose by Serianni's modified Kiliani-Fischer reaction in 20 and 39% yield, respectively. Exposure to NaOH and phenylboronic acid converted the D-[1-13C]mannose into a chromatographically separable 1:1:8 mixture of D-mannose, D-glucose, and D-fructose with retention of the label at C-1. D-[x-13C]Fructose (x = 1 or 2) was obtained in 80% yield from D-[x-13C] glucose by use of immobilised glucose isomerase in the presence of sodium germanite to complex the fructose. In addition, [2-13C]dihydroxyacetone was synthesised from [2-13C]fructose by consequential methanolysis, periodate oxidation, borohydride reduction, and acid hydrolysis.
L-Sorbose has been converted to L-fructose via the key-intermediate (9) (Scheme 3), available in >80% yield by acetonation of L-sorbose with dimethoxymethane and SnCl2 in dimethoxyethane. The synthesis of 3,4;5,6-di-O-isopropylidene-D-glucitol and 2.3 ; 4.5-di-O-isopropylidene-aldehvdo-D-arabinose from D-glucono-1,5-lactone is referred to in Chapter. An improved process for the isolation of D-fructose from the acid hydrolysate of sucrose involves formation of a double salt with Ca(OH)2, followed by decalcification and purification.
2.3 Higher Sugars. – Reaction of isopropylidene-D-glyceraldehyde with triphenyl(propionylmethy1ene)phosphorane afforded the isomeric enuloses (10) and (11) which were separated by chromatography. Hydroxylation then gave access to the four diastereomeric 1,2-dideoxy-3-heptulose derivatives (12)-(15) (Scheme 4). A recently developed route to higher sugar allylic alcohols (see Vol. 20, p. 8) has been exploited in connection with the attempted synthesis of desazatunicamine. It involves coupling of two monosaccharide units derived from D-galactose and D-ribose, respectively, via an additional carbon atom, as shown in Scheme 5. The stereoselectivity of the zinc borohydride reduction of compound (16) and similar higher sugar enones implies complexation of the ring and the carbonyl oxygen atoms with zinc ion in accordance with the Cram cyclic model for 1,2-asymmetric induction, and the steric course of the osmylation of higher sugar enones and allylic alcohols such as compounds (16) and (17) is rationalised in terms of Kishi's rule.
3 Analytical Methods
A colorimetric assay for glucose in the presence of fructose, based on the selective reduction of ketoses by sodium borohydride and CeCl3 has been developed. An analytical method for the determination of fructose and other ketoses in the presence of aldoses, sucrose, and insulin is mentioned in Chapter 22. In h.p.l.c. separations, reducing sugars may be detected fluorometrically after post-column reaction with 2-cyanoacetamide. The fluorescent species derived from glucose have been identified as the pyrrolidine derivative (19) and the pyridine derivative (20) formed, presumably, as indicated in Scheme 6, from the dehydrated Knoevenagel adduct (18) and its 4-deoxy-5-hydroxy-isomer by cyclisation, further dehydration and, in the case of product (20), reduction. The dienamide (18) itself is strongly u.v. absorbing and susceptible to electrochemical oxidation, which might permit additional methods of detection.
A D-glucose-sensitive electrode has been constructed by coating of a platinum electjrode with a cross-linked poly(vinylalcohol) layer containing immobilised D-glucose oxidase and ferrocene.
Physical Measurements
The solubilities of D-xylose and D-mannose in aqueous ethanol (0-100%) at 25°C have been measured by use of refractometry and h.p.l.c., and some physical properties (m.p., solubilities) of crystalline anhydrous α-lactose, α,β-lactose, and β-lactose have been reported. The excess Gibbs free energies of aqueous solutions of carbohydrates and other polyols at 25°C have been determined and correlated with the sugar configurations. The standard enthalpy of formation (1263.4 [+ or -] 1.2 kJmol-1) of α-D-mannose at 298.15 K has been calculated from the corresponding standard energy of combustion (-15.6123 [+ or -] 0.0065 kJg-1) which was measured by use of precision static oxygen bomb calorimetry.
The catalytic activity of hydrated metal sulphates in the mutarotation of D-glucose has been examined, and the relations between logKa, ΔH, and ΔS of the reaction and the parameters of the metal ions, were discussed.
The apparent molal volumes and molal compressibilities of several monosaccharides, disaccharides and methyl pyranosides in dilute aqueous solution have been studied at 5, 15, and 25°C. The results were discussed in the light of solute-solvent interactions and a model for the hydration of galactose and lactose was proposed. The molal volumes of small carbohydrate molecules have been measured in an attempt at elucidating the relationship between molecular properties and sweetness. Molal volumes reflect fine differences in structure e.g.. axial or equatorial disposition of particular hydroxy groups) which are in turn related to differences in taste. In order to interpret differences in sweetness the viscosimetric constants and the heats of dilution of three monosaccharides, three disaccharides and the very sweet chlorinated sugar (21) have been determined, and their i.r. and Raman spectra have been recorded. The osmotic pressures of aqueous glucose, sucrose, and raffinose solutions have been calculated from their freezing point depressions. To obtain the apparent volumes of the hydrated species (0.1865, 0.3525, and 0.5105 nm3, respectively) their partial molal volumes were determined together with the partial molal volumes of the water of their solutions.
The u.v. and i.r. spectra of oligomeric acid products from the alkaline degradation of fructose and glucose have been evaluated. E.s.r. measurements on γ-irradiated crystals of α- and β-D-glucose hydrate confirmed that the structures of the primary paramagnetic centres derived from the hydrated species differ from those from the anhydrous analogues. The existence of several novel free radicals is reported. 13C-n.m.r. spectroscopy has been used to determine the anomeric configuration and the ring-size of D-fructose obtained from sucrose by the action of yeast and Candida utilis invertases. The hydrolysis was complete within 5 min yielding initially β-fructofuranose almost exclusively. After 60 min a mixture containing 74% β-fructopyranose, 22% β-furanose and 3.8% α-furanose had formed.
Isomerisation
The epimerisation of aldoses by metal complexes of alkylenediamines with long N-alkyl substituents has been reported. In a study involving various ligands, N,N'-dialkylethylenediamines showed the highest activity for épimérisation of glucose at C-2, equilibrium being reached within a few minutes under mild conditions. The equilibrium was shifted towards glucose by the more hydrophobic ligands with longer M-alkyl chains. Molybdate ions in aqueous solution at 90-125°C catalysed the isomerisation of D-glucose to a 3:1 mixture of D-glucose and D-mannose. At 120-150°C a mixture of D-glucose, D-mannose, D-allose, and D-altrose was obtained from which the first two sugars were removed by yeast fermentation leaving D-allose and D-altrose (3:2) in 14-17% yield. Several epimerisation reactions are mentioned in Section 2 of this Chapter.
The Ca(OH)2 promoted anomerisation of D-glucose has been studied by 13C-n.m.r. spectroscopy. The degree of anomerisation was found to vary with the Ca(OH) 2 concentration and it is thought that Ca2+ ions bind to O-1 and O-3 of the α-pyranose anomer, whereas in the β-anomer O-1 and O-2 are involved in complexation.
(Continues...)
Excerpted from Carbohydrate Chemistry Volume 22 by R. J. Ferrier. Copyright © 1990 The Royal Society of Chemistry. Excerpted by permission of The Royal Society of Chemistry.
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5.2 The dispatch costs that are incurred are not included in the purchase price. They can be viewed by clicking the appropriate button on our website or in the respective quote, are shown separately over the course of the order transaction and must additionally be borne by you, insofar as free delivery is not confirmed.
5.3 The payment methods that are available to you are shown by clicking the appropriate button on our website or are disclosed in the respective quote.
5.4 Unless otherwise specified for the respective payment methods, the payment claims arising from the contract that has been concluded become payable immediately.
- Delivery conditions
6.1 The delivery conditions, delivery date and existing supply restrictions, if applicable, can be found by clicking the appropriate button on our website or in the respective quote.
Unless a different period is specified in the item description or our delivery conditions, the goods are delivered within 3-5 days after the conclusion of the contract (in case an advance payment has been agreed upon, after the payment authorisation).
6.2 If you are a consumer, the following is statutorily regulated: The risk of the sold item accidentally being destroyed or degraded during shipping only passes over to you when the item in question is delivered, regardless of whether or not the shipping operation is insured. This condition does not apply if you have independently commissioned a transport company that has not been specified by us or a person who has otherwise been appointed to execute the shipping operation.
If you are a businessman, the delivery and shipping operations take place at your own risk.
- Statutory warranty right
Liability for defects is governed by the “Warranty” provisions in our General Terms and Conditions of Business (Part I).
last update: 01.01.2022
Data protection declaration
Unless stated otherwise below, the provision of your personal data is neither legally nor contractually obligatory, nor required for conclusion of a contract. You are not obliged to provide your data. Not providing it will have no consequences. This only applies as long as the processing procedures below do not state otherwise.
“Personal data” is any information relating to an identified or identifiable natural person.
Responsible person
Contact us at any time. The contact details of the person responsible for data processing can be found in our legal notice.
Collection, processing, and transfer of personal data in orders
When you submit an order we only collect and use your personal data insofar as this is necessary for the fulfilment and handling of your order as well as processing of your queries. The provision of data is necessary for conclusion of a contract. Failure to provide it will prevent the conclusion of any contract. The processing will occur on the basis of Article 6(1) b) GDPR and is required for the fulfilment of a contract with you.
Your data is transferred here for example to the shipping companies and dropshipping providers, payment service providers, service providers for handling the order and IT service providers that you have selected. We will comply strictly with legal requirements in every case. The scope of data transmission is restricted to a minimum.
Duration of storage
After contractual processing has been completed, the data is initially stored for the duration of the warranty period, then in accordance with the retention periods prescribed by law, especially tax and commercial law, and then deleted after the period has elapsed, unless you have agreed to further processing and use.
Rights of the affected person
If the legal requirements are fulfilled, you have the following rights according to art. 15 to 20 GDPR: Right to information, correction, deletion, restriction of processing, data portability. You also have a right of objection against processing based on art. 6 (1) GDPR, and to processing for the purposes of direct marketing, according to art. 21 (1) GDPR.
Right to complain to the regulatory authority
You have the right to complain to the regulatory authority according to art. 77 GDPR if you believe that your data is not being processed legally.
Right to object
If the data processing outlined here is based on our legitimate interests in accordance with Article 6(1)f) GDPR, you have the right for reasons arising from your particular situation to object at any time to the processing of your data with future effect.
If the objection is successful, we will no longer process the personal data, unless we can demonstrate compelling legitimate grounds for the processing that outweigh your interests or rights and freedoms, or the processing is intended for the assertion, exercise or defence of legal claims.
last update: 10.01.2022