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The Action of Ammonia on Carbohydrates and Related Carbonyl

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The Action of Ammonia on Carbohydrates and Related Carbonyl Copyright is owned by the Author of the thesis. Permission is given for a copy to be downloaded by an individual for the purpose of research and private study only. The thesis may not be reproduced elsewhere without the permission of the Author. 11THE ACTION OF AMMONIA ON CARBOHYDR.li.TES .AND RELli.TEO CARBONYL COMPOilliDS11 A thesis presented in partial fulfilment of the requirements for the degree of Doctor of Ph i losophy at Ma ss ey University of lvla na wat u, Pa lmerston No rth, Ne w Zeala nd. ROSS GR I MMETT MUR..TUI.Y 1965 Chromatogram shmving IILlidazoles fo�emerl :f'x•om: to Paper (IJ R) ( i) Imidazole (marker); ( ii) GlycePaldehyde/tTH"'; ( i ii) Pyruvaldehyde/I' TH�; ( v) Dihvd�oxvacetonel'NH,.; (v-) j:r<:- i Eydroxy:pyrl..rvaldeh;y("J_e :s:3 ; andu (vi)" Imidazo.1e �marker) .. ACKNOWLEDGEMENTS The author wishes to thank Dr . E.L. Richa rds , Dr . R.W. Ba iley and Dr . Hawke for their J.C. advic e and encouragement. ( i ) ABSTR..A.CT The chromatography of imida .zoles has been studied and a me thod developed for their quantitative estimation. The following fa ct s ha ve been brought to light :- ( i ) Formaldehyde does not form imidazoles at room temperature in ammoniacal solut ion. ( ii) From the complex mi xture result ing from the intera ction ' of glyoxal wi th aqueous ammonia imidazole and 2,2 -bis­ imidazole ha ve been isolated and identified, whi le 2-formyl ­ imida zole ha s been tentatively identifi ed. ( iii ) Glycolaldehyde reacts wi th aque ous ammonia to form imidazole and 2- hydroxymethyl imidazole . ( iv) DL-Glyceraldehyde reacts with aqueous ammonia to form a co mplex mixture of neutral and basic co mpounds . Dihydroxy­ acetone , glucose, fructose, mannose, arabinose, lyxose and xylose ha ve been tentatively identified by paper chromatography whi le ribose wa s suspected in low concentration. 2-Hydro xy­ me t hy a--4 ( 5 ) -methylimidazole , 4 ( 5 ) -methyl imida zole, 4 ( 5 ) ­ ( 2- hydroxyethyl ) imidazole and 4 ( 5 ) -hydroxymethylimidazole ha ve been isolated and characterised, and their orders and ra tes of forma tion studied. ( v ) Py ruva ldehyde reacts exothermically with concentrated ammonia solution to form four imidazolic compounds . Three of these ha ve been isola ted and cha ra cterised as 2-acetyl- ( ii) 4 ( 5 ) -methylimida zole, 2,4( 5 ) -dimethyl imidazole and 4 ( 5 ) -methyl- imidazole. The latter two compounds were formed in approx- imately equimolecul ar proportions . These results fa il to ' confirm Bern hauer s finding tha t pyruva ldehyde cannot act as a source of formaldehyde in imidazole forma tion. ( vi ) Hydroxypyruva ldehyde browns rapidly in aqueous ammonia forming 2-hydroxymethyl-4 ( 5 ) -m ethyl imidazole, 4 ( 5 ) -methyl- imidazole and 4 ( 5 ) -hydroxymethyl imidazole. The yields of the lat ter two compounds have been found to be higher than from a simi lar mixtur e of di hydroxya cetone with a�monia . ( vii ) Both di acetyl and acetoin react with ammonia to form 2,4, 5-trimethyl im ida zole. ( viii) 4 ( 5 ) - ( 2-Hydroxye thyl ) imida zole ha s been tentatively identified from the mixture resulting fro m the interaction of 1, 4-dihydroxybutan-2-one with aqueous ammonia . ( ix) Arab inose reacts wi th aqueous ammonia to form a complex mi xture of imidazoles from which 4 ( 5 ) -methylim ida zole ha s be en isolated and identified . ( x ) A chromatographic study has been carri ed out to determine the orders of forma tion of imidazoles resulting from the interactions of a number of carbohydra tes and their degrada tion products with aqueous ammonia . Ar ising from this study have come the following ma in results:- ( a ) It appears that, contrary to the findings of Komo to , a number of imidazoles wi th lo w R values prob ably polyhydroxy- f ( ( iii ) alkyl-substituted ) are formed more ra pidly than 4 ( 5 ) -methyl­ imidazole from hexo se suga rs with a��onia. (b ) Differently linked reduc ing di saccha rides give ma rk­ edly different pa tterns of imidazoles under ammoniacal condi tions. (xi ) As a re sult of (b ) above, a micro-method ha s been developed for determina tion of the position of the glycosidic link in reduc ing hexo se disaccharides and ho mo geneously-linked oligo­ saccharides . (iv) OF CONTENTS TABLE ABSTRACT (i) INTRODUC'l'ION 1 I. The Chemistry of the Imidazoles 4 10 II. The Alkaline Degradation of Carbohydrates \ III. The Reaction of Ammonia with Carbonyl Compounds 17 IV. The Interaction of Other Hitrogenous Bases with Sugars and their Fission Products 32 References 38 RESULTS DISCUSSION AlfD I. The Chromatography of Imidazoles 43 II. Separation and Quantitative Determina tion of Imidazoles, 51 III. Reaction of a-Dicarbonyl and a-Hydroxycarbonyl Compounds with Aqueous Ammonia 55 i) Formaldehyde/a�monia 55 ii) Glyoxal/aw..monia 56 iii) Glycolaldehyde/a��onia 64 iv) DL-Glyceraldehyde/ammonia 69 v) Pyruvaldehyde/ammonia 85 vi ) Hydroxypyruvaldehyde/ammonia 95 vii) Diacetyl/ammonia 103 viii) Acetoin/ammonia 105 ix) 1,4-Dihydroxy-2-butanone/ammonia 106 l(x) L-.�abinose/ammonia 110 ( xi ) Reactions of Carbohydrates and Some Degrad­ ation Products with Ammonia IV. Linkage Identification in Hexose Disaccharides by Formation of Imidazoles 127 Future projects 143 References 144 EXPERIMENTAL 149 Ia. Synthesis of Imidazoles 150 Ib . Chromatography of Imidazoles 166 II. Separation and Quantitative Determination of Imidazoles 168 III. The Reaction of a-Dicarbonyl and a-Hydroxycarbon- yl Compounds with Aqueous Ammonia 180 (i) Formaldehyde/aw�onia 180 (ii) Glyoxal/ammonia 181 ( v ) ( iii ) Gl yc olaldehyde/ammonia 184 ( iv) DL- Glycera ld ehyde/ammonia 187 ( v ) Pyruvaldehyde/ammonia 198 ( vi ) Hydroxypyruva ldehyde/ammonia 208 ( vii ) Diacetyl/ammonia 214 ( viii ) Ac etoin/ammonia 216 ( ix) 1,4-Dihydroxy-2-butanone/ammonia 217 ( x ) L-Arab inose/ammonia 221_ ( xi ) Reactions of Ca rb ohydrates with -�mmonia ( Su rvey) 222 IV. Ivii crotecJ:ulique for Linkage Determination in Reducing Hexose Di saccharides 224 References 226 APPENDIX- Sp ectroscopy of Imidazoles 229 (vi ) LIST OF TABLES INTRODUCTION TABLES �. Imidazoles f'rom Carbohydrate/ammonia Mixtures Pyra zine and Pyridine Derivatives f'rom Sugar/ 25-6 2. ammonia Mixtures 28 RESULTS DISCUSSION TABLES A.liD C� Chromatographic Da ta f'or Imidazoles on Paper 45 11 11 11 on Cellulose TLC 47 C2 C3 tt 11 11 on Silica Alumina &TLC 48 1. Sugars present in Glyceraldehyde/aw�onia mixtu�e 71 Yields of 4(5)-Liethylimidazole f'rom Pyruvaldehyde 2. under various conditions 92 Yields of Imidazoles f'rom Hydroxypyruvaldehyde and 3. Dihydroxyacetone in Arnmoniacal Solutions 99 4. Time Study of Reactions between Carbohydrates and Aw�onia 112-7 5. Rim values of major imidazolic products from reducing hexose disaccharides with ammonia 132 6. Times of appearance of characteristic imidazole patterns from maltodextrin and isomaltodextrin series with ammonia 134 EXPERIMENTAL TABLES El values of imidazoles on No . paper 170 Rim 3MT"� E2 Optimum reading times , wavelengths of maxima and A 1\ 172 absorbances at max and 480 Replicate determina tions of absorbances 174 E3 Recoveries of imidazoles from Whatman No. 3MM E4 paper 177 E5 values and colour reactions of products from Rf' Glyceraldehyde/awJnonia 187 Chromatographic data for pyruvaldehyde/ammonia E6 mixture 199 (vii) LIST OF FIGURES PLATES Al'ill Chromatogram showing Imidazoles from Pyruv­ aldehyde, Hydroxypyruvaldehyde, Glycer­ aldehyde and Dihydroxyacetone in .�mon- iacal Solution. Frontispiece RESULTS AND DISCUSSION FIGURES Cl �To-dimensional T.L.C . of imidazoles on alumina 50 1. IR spectrum of glycosine before 57 2. IR spectra of imidazole and compound (R 1.00) from Glycolaldehyde/aE,monia before 64 im 3. IR spectra of 1-benzylimidazole and 1-benzyl-2-hydroxymethylimidazole before 65 4. Browning of Glyceraldehyde in ammonia at 37° before 69 5. IR spectra of picrates of : (i) 2-methyl-4(5)-hydroxymethylimidazole (ii) comp m..md (R 1.37) from glyceraldehyde/ . I m ammonJ.a ( iii) 2-hyclroxymethyl-4( 5 )-methylimidazoJ.e before 73 p.m.r. spectrum (D 0) of 4(5)-hydroxy- 6. 2 methylimidazole 80 7. Rate of formation of imidazoles from glyceraldehyde/ammonia 83 8. IR spectrum of 2-acetyl-4(5)-methylimidazole before 87 p.m.r. spectra of 2,4,5-trimethylimidazole 9. { D 0) , 4(5)-methylimidazole and 2-acetyl- 2 4(5)-methylimidazole (CDC1 and D 0) before 88 3 2 10. IR spectra of picrates of 2,4(5)­ cUmethJrlimidazole and compound (R 1.57) 1 m from pyruvaldehyde/an�onia before 91 11. IR spectra of picrates of 4(5)-methyl­ imidazole and compound (R �.29) from I m pyruvaldehyde/ammonia before 92 PLATES 1. Imidazole patterns from disaccharides and an�onia 130 2 and Imidazole patterns from substituted 3. glycosides and ammonia �33 133A & EXPERIMENTAL PIGURES 1. Standard curves for analysis of imidazoles before 171 2. Reproducibility experiment 173 3. Absorption spectra for imidazoles with diazotised sulphanilic acid before 175 ( vi ii) PIGURES Ab sorption specti'a for imidazoles -vvith di az o 4. p-toluidine before 178 5. Standar d curves with diaz o p-toluidine before 178 6. " 11 t1 11 p-bro moani ine before 179 1 7 • 11 11 u " rr of imidazoles eluted fr om Wha tman Ho . :paper before 179 3I�Eit APPEliDIX Line IR spectra of imi dazoles before 230 INTRODUCTION INTRODUCTION Although the interaction of carbohydrates with ammonia has been intensively studied 44 ' 49 ' 55-6 ' 70-1' 100-1 the · mechanisms of many of the complex reactions involved remain obscure. It has proved difficult, and at times impossible, to identify sugar breakdown products in ammoniacal medium, but a knowledge of the nature of the imidazolic compounds formed in such reactions is of assistance in the prediction of the structures of these carbohydrate fragments.
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