160. The iodine-catalysed conversion of sucrose into 5-hydroxy-methylfurfuraldehyde

Bonner, T. G.; Bourne, E. J.; Ruszkiewicz, M.

doi:10.1039/jr9600000787

Cited by 34 publications

(13 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For sugar derivatizations, alditol acetate derivatives were prepared according to Albersheim et al [ll]; demethylation was performed according to Bonner et al [12].…”

Section: Miscellaneous Analytical Techniquesmentioning

confidence: 99%

Structure of the major triglycosyl phenol‐phthiocerol of Mycobacterium tuberculosis (strain Canetti)

Daffé

Lacave

Lanéelle

et al. 1987

European Journal of Biochemistry

132

102

View full text Add to dashboard Cite

Phenol-phthiocerol glycolipids have been found previously in Mycobacterium leprae, M . kansasii, M. bovis and M . marinum, but not in M . tuberculosis. A search for such glycolipids in this latter species showed that the Canetti strains of M . tuberculosis synthesize a major triglycosyl phenol-phthiocerol, accompanied by minor amounts of other glycolipids with a similar aglycone moiety.The triglycoside moiety has the following structure: 2,3,The aglycone moiety consists in phenol-phthiocerol (two homologs). Its two secondary alcohol functions are esterified by mycocerosic acids (homologs with 26-32 carbon atoms and with 2 -4 methyl branches). The proposed structure differs on several points from the M . leprae glycolipids, but presents some analogy with the major glycolipid of M. kansasii.A minor monoglycosyl phenol-phthiocerol was also studied. Its overall structure is very similar to that of M . bovis, with 2-0-methyl rhamnose as sugar moiety.In the last few years, it has been realized that glycolipids are major surface antigens of pathogenic mycobacteria [l], and important applications are expected from this: the detection and identification of bacteria in patients and the elaboration of semi-synthetic vaccines.Three phenol-phthiocerol trisaccharides isolated from Mycobacterium leprae have attracted much attention, since they were the first antigens to be chemically defined in this important pathogen [l -31.Long ago, phenol-phthiocerol monosaccharides were identified in M . bovis [4], M. marinum [5] and M . kansasii [6]; the structure of the glycolipid of the latter species has been revised recently [7, 81. The four mycobacteria quoted above, as well as M . tuberculosis, are pathogenic for man and have the same kind of mycolic acids in common [9]. However no phenol-phthiocerol glycolipid had been found previously to this paper in the most important pathogen of this genus, M . tuberculosis. We searched for glycolipids in various strains belonging to this species, and a major phenol-phthiocerol trisaccharide, accompanied by minor amounts of a phenol-phthiocerol monosaccharide, was detected in the four Canetti strains of M. tuberculosis tested. The structure of the triglycosyl glycolipid is described here. It differs on several points from the glycolipids of M . leprae, and presents some analogy with the major glycolipid of M. kansasii.

show abstract

“…For sugar derivatizations, alditol acetate derivatives were prepared according to Albersheim et al [ll]; demethylation was performed according to Bonner et al [12].…”

Section: Miscellaneous Analytical Techniquesmentioning

confidence: 99%

Structure of the major triglycosyl phenol‐phthiocerol of Mycobacterium tuberculosis (strain Canetti)

Daffé

Lacave

Lanéelle

et al. 1987

European Journal of Biochemistry

132

102

View full text Add to dashboard Cite

show abstract

“…Bonner et al 24,25 using this method, converted sucrose into HMF in 20% yield. Morikawa 26 utilised iodine as a catalyst to obtain HMF in 64% yield.…”

Section: The Kinetics Of the Hmf Synthesismentioning

confidence: 99%

“…Non-aqueous solvents require high dilution system; owing to the hydrophilic character of reagents. Various solvents were tested: Bonner 24,25 and Shur et al 46 carried out the reaction in DMF, Brown 47 -in acetonitrile. Morikawa 26 proposed the application of quinoline and Smythe and Moye 48,49 performed the reaction in polyglycol ethers.…”

Section: The Kinetics Of the Hmf Synthesismentioning

confidence: 99%

Synthesis, chemistry and applications of 5-hydroxymethyl-furfural and its derivatives

Lewkowski¹

2001

Arkivoc

415

144

View full text Add to dashboard Cite

“…One could also focus on one particular compound, such as 5-HMF [9], which could arise from dehydration of fructose, from glucose, or cellulose [10]. 5-HMF could also be further decomposed into oximes [11], phenylhydrazone [12], p-nitrophenylhydrazone [13], semioxamazone [14], semicarbazone [15], or azine [16]. Concerning this particular compound, the question is: what proportion of 5-HMF present in meat after the grilling process is due to Maillard reactions, and how much is due to other processes?…”

Section: Meet the Maillard And Grilled Steak Challengementioning

confidence: 99%

Maillard and grilled steak challenge

This

2015

Anal Bioanal Chem

View full text Add to dashboard Cite

show abstract

160. The iodine-catalysed conversion of sucrose into 5-hydroxy-methylfurfuraldehyde

Abstract: Bonner, Bourne, and Ruszkiewicz. 787160. The lodine-catalysed Conversion of Sucrose into 5-Hydroxymeth ylfurfuraldeh yde.

Cited by 34 publications

References 0 publications

Structure of the major triglycosyl phenol‐phthiocerol of Mycobacterium tuberculosis (strain Canetti)

Structure of the major triglycosyl phenol‐phthiocerol of Mycobacterium tuberculosis (strain Canetti)

Synthesis, chemistry and applications of 5-hydroxymethyl-furfural and its derivatives

Maillard and grilled steak challenge

Contact Info

Product

Resources

About