9-Glucosyl derivative

Table 1 Relative sweetness intensity of various glucosyl derivatives 26-29 of stevioside [62]...

The identity of a glucosylated derivative of L-biopterin from Synechococcus sp. PGG 7942 has been confirmed as the 2 -0-a-glucosyl derivative by 2-D NMR spectroscopy <2001PTR121>. Tetrahydro-D-monapterin 223 has been identified as the native pteridine in Tetrahymena pyriformis <2001HGA918> the configuration and stmcture were confirmed by comparison with synthetic samples of known configuration. 

Further enzymatic modifications allowed the isolation of the glucosylated derivatives 12a (60 times more soluble than 12) and of the acid derivative 12b, which was three orders of magnitude more soluble [35]. 

Lupinus luteus (29,30). Cytokinins also occur naturally at the ribonucleoside and ribonucleoside phosphate levels (31,32,33) and exogenously applied cytokinins have been shown to undergo metabolism to glucosyl derivatives (34,35,36,37,38). 

As for the amine moiety, the rearrangement has been demonstrated (although not unequivocally in all cases) for mono-A -substituted glycosyl-amines derived from aromatic amines and aralkyl- and alkyl-amines and for di-A-substituted glycosylamines containing dialkyl, alkyl-aryl, aralkyl, isocyclic, and heterocyclic alkyl radicals. The rearrangement has been reported for A-glucosyl derivatives of amino acids, but not as yet... 

The 2-phenylsulfinyl glucal 111 is available from glucal 110 by addition of phenylsulfenyl chloride, DBU elimination and oxidation. The Cl-substituted glycal 113, obtained by addition of the lithium reagent 112 to aldehydes, is transformed to a 8-D-C-glucosyl derivative 114 by reductive removal of the phenylsulfinyl group with Raney nickel and stereoselective hydration of the C/C double bond by hydroboration-oxidation. 

Sweetness quality and intensity of various glucosyl derivatives of stevioside... 

These generalizations are illustrated by the recent synthesis of L-ascorbic acid glucosides 11 and 12 (16), The monosodium salt of ascorbic acid in N,N-dimethylformamide (DMF) affords exclusively the 03 monoalkylated derivative 9 on alkylation with 2,3,4,6-tetra-O-a-n-glucopyranosyl bromide. To obtain the 02 glucosylated derivative 10, under the same conditions, required the protection of the C3 hydroxyl as a methyl ether. Several workers have reported the biosynthesis of ascorbic acid glucosides in bacteria (17) however, the structure and position of glucosylation in these compounds has not been unambiguously determined. 

Barbiturate Parent Hydroxy Derivatives N-Glucosyl Derivatives Carboxylic Acids... 

The 4-0-glucosamine unit of paromomycin was replaced with glucose, mannose and galactose, with only the glucosyl derivative retaining activity. ... 

The revised structure of validamycin A 85 (compounds 85-02 see pg. 320) was reported by Suami, Ogawa, and Chida [90] in 1980 and it turned to be 4-0-)8-d-glucopyranosyl validamycin A, instead of the 3-O-glucosyl derivative previously reported by Kameda in 1972. 

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