Alan Haines

School Position: Reader Emeritus
Room: 3.02
Telephone: (01603) 592708

After PhD studies at the University of Birmingham, Dr Haines spent post-doctoral periods in the USA and Germany, after which he held a CIBA research fellowship at the University of Sussex prior to joining the School of Chemical Sciences at UEA.  He spent periods of sabbatical leave in Canada, at the University of Edmonton in Alberta and at Queen's University in Kingston Ontario, and taught in France and Brazil.  He is the author of two books on 'Methods for the Oxidation of Organic Compounds' and has translated from German a research monograph on the structure and biology of carbohydrates.  He has published widely in research journals and in review literature on carbohydrate chemistry, and after retirement in July 2000 has continued to work 'at the bench' within the School.

Research interests

A major interest is the chemistry of carbohydrates, and in their selective reactivity which enables preparation of novel derivatives. For example, 'tail to tail' linked disaccharides were synthesised, sugars which are not joined in the usual manner 'head to tail' (as in maltose) or 'head to head' (as in trehalose) [1a,1b]. A report that a compound (named coyolosa) of this unusual type occurred naturally led to increased interest in such novel disaccharides.

The synthesis and testing of the mirror image form of the important disaccharide trehalose was carried out [2a,2b] in order to investigate the mode of action of the natural disaccharide in stabilisation of biomolecules, a property with considerable potential for storage of hormones, drugs, vaccines and other biologically important materials of commercial interest. Interestingly, a distinct difference in the stabilising ability of the enantiomers was observed.

Exploration of the use of liquid carbon dioxide as a solvent for “green chemistry” led to an examination [3] of factors which govern the solubility of organic compounds in this solvent, and also to an attempt to rationalise our findings [4a, 4b, 4c].

Crystal structures of bisulphite addition products of D-galactose [5a], D-glucose [5b], dehydro-L-ascorbic acid [5c], D-ribose [5e], D-lyxose [5f and 5g] and D-mannose [5h] have been determined, and new information obtained on factors affecting the conformations tartaric acid derivatives by measurement of the crystal structure of an acetal of tartaronitrile [5d].  The crystal structures of aryl ribosylamines obtained in research towards bio-active glycosides have been determined (5i).

In collaborative research initiated by an interest in molecular recognition between carbohydrates and carbohydrate binding proteins (lectins), the change in light absorption of gold sols, modified by a self-assembled monosaccharide layer, on interaction with a lectin specific for that carbohydrate has been used for quantitative detection of a lectin [6]. In an extension of this use of modified gold nanoparticles, the favourable interaction between lactose and calcium ions has been used to illustrate the measurement of biologically relevant carbohydrate-carbohydrate interactions mediated by metal ions [7], and silver and gold nanoparticles have been evaluated and compared for colourimetric bioassays [8].

Selected publications  

(1a) 'Evidence on the structure of coyolosa. Synthesis of 6,6 -ether linked hexoses'
A. H. Haines, Tetrahedron Lett., 2004, 45, 835-837.

(1b) 'Synthesis of 6,6'-ether linked disaccharides from D-allose, D-galactose, D-glucose and D mannose; evidence on the structure of coyolosa'
A. H. Haines, Org. Biomol. Chem., 2004, 2, 2352-2358.

(2a) 'Synthesis of L-trehalose and observations on isomer and by-product formation'
A. H. Haines, Carbohydr. Res., 2003, 338, 813-818.

(2b) 'Non-equivalence of D- and L-trehalose in stabilising alkaline phosphatase against freeze-drying and thermal stress. Is chiral recognition involved?'
A. H. Haines, Org. Biomol. Chem., 2006, 4, 702-706.

(3) 'Solubility dependence of peracylated D-glucopyranoses in supercritical carbon dioxide on the structure of their acyl moieties'
A. H. Haines, D. C. Steytler, and C. Rivett, J. Supercrit. Fluids, 2008, 44, 21-24.

(4a) 'The crystal structures of 1,2,3,4,6-penta-O-trimethylacetyl- and 1,2,3,4,6-penta-O-dimethylacetyl-ß-D-glucopyranose'
A. H. Haines and D. L. Hughes, Carbohydr. Res., 2007, 342, 2264-2269.

(4b) 'Benzene-1,3,5-triyl triacetate'
A. H. Haines and D. L. Hughes, Acta Cryst. 2009, E65, o3279.

(4c) 'Benzene-1,3,5-triyl tris(2,2-dimethylpropanoate)'
A. H. Haines and D. L. Hughes, Acta Cryst. 2009, E65, o3280.

(5a) 'The crystal structure of potassium (1S)-D-galactit-1-ylsulfonate'
A. H. Haines and D. L. Hughes, Carbohydr. Res., 2010, 345, 2705-2708.

(5b) 'Sodium (1R)-D-glucit-1-ylsulfonate monohydrate'
A. H. Haines and D. L. Hughes, Acta Cryst. 2012, E68, m377-m378.

(5c) 'Potassium (1R,4R,5S,8S)-4,5,8-trihydroxy-3-oxo-2,6-dioxabicyclo[3.3.0]octane-4-sulfonate dihydrate'
A. H. Haines and D. L. Hughes, Acta Cryst. 2013, E69, m7-m8.  
doi.org/10.1107/S1600536812048672.

(5d) '(4S,5S)-2,2-Dimethyl-1,3-dioxolane-4,5-dicarbonitrile'
A. H. Haines and D. L. Hughes, Acta Cryst. 2013, E69, o1104.
doi.org/10.1107/S1600536813015973.

(5e) ‘Crystal structure of potassium (1R )-D-ribit-1-ylsulfonate’
A. H. Haines and D. L. Hughes, Acta Cryst. 2014, E70, 406-409.
doi.org/10.1107/S1600536814022685

(5f) 'Crystal structure of potassium (1S)-D-lyxit-1-ylsulfonate monohydrate'
A. H. Haines and D. L. Hughes, Acta Cryst. 2015. E71, 993–996.
doi.org/10.1107/S2056989015014139

(5g) 'Crystal structure of sodium (1S)-D-lyxit-1-ylsulfonate'
A. H. Haines and D. L. Hughes, Acta Cryst. 2016. E72, 628–631.
doi.org/10.1107/S2056989016005375

(5h) 'Crystal structure of sodium (1S)-D-mannit-1-ylsulfonate'
A. H. Haines and D. L. Hughes, Acta Cryst. 2018. E74, 1314–1318.
doi.org/10.1107/S2056989018011556

(5i) 'Synthesis of N-(2,4-dinitrophenyl) derivatives of D-ribosylamines; unexpected reaction and hydrolysis products'
C. E. Anson, J. C. Briggs, A. H. Haines and M. Molinier, Carbohydr. Res., 2022, 516, 108564.

With the senior author D. A. Russell:

(6) 'Rapid quantitative colorimetric detection of a lectin using mannose-stabilised gold nanoparticles'
D. C. Hone, A. H. Haines and D. A. Russell, Langmuir 2003, 19, 7141-7144.

(7) 'Gold Glyconanoparticles for Mimics and Measurement of Metal Ion-Mediated Carbohydrate-Carbohydrate Interactions'
A. J. Reynolds, A. H. Haines, and D. A. Russell, Langmuir 2006, 22, 1156-1163

(8) 'Silver and Gold Glyconanoparticles Colourimetric Bioassays’
C. Schofield, A. H. Haines, R. A. Field, and D. A. Russell, Langmuir 2006, 22, 6707-6711.

(9) 'Targeted photodynamic therapy of breast cancer cells using lactose-phthalocyanine functionalized gold nanoparticles'
P. G. Calavia, I. Chambrier, M. J. Cook, A. H. Haines, R. A. Field, D. A. Russell, J. Colloid Interface Sci. 2018, 512, 249–259