The saccharide–hydrazide linkage: molecular and crystal structures of the semicarbazide derivatives of d-glucose, d-galactose, and d-xylose, including a ‘forbidden’ conformation of the galactose derivative
The X-ray crystal structures of the semicarbazide derivatives of D-glucose, D-galactose, and D-xylose are described. All are glycopyranosyl derivatives in the solid state. The glucose semicarbazide crystallizes as a dihydrate. Two different conformations of the galactose semicarbazide are found, one having the gg side-chain orientation unfavorable for monosaccharides having the 4C(1)-D-galacto configuration. In the two other known examples, this conformation is stabilized by an intramolecular hydrogen bond, but in the current structure, the hydrogen bonds involving the side chain are intermolecular. In these semicarbazides the N [bond] N [bond] C[double bond] O torsional angle is approximately 180 degrees, in contrast to the angles of 0.60 and 13.9 degrees in the two solid-state conformations of 2-benzoyl-1-(alpha-D-xylopyranosyl)hydrazine [Ernholt, B. V.; Thomsen, I. B.; Lohse, A.; Plesner, I. W.; Jensen, K. B.; Hazell, R. G.; Liang, X.; Jakobsen, A.; Bols, M. Chem. Eur. J. 2000, 6, 278-287]. The water molecules and the carbonyl oxygen are heavily involved in H-bonding.
Pharmacology, Toxicology and Pharmaceutical Science
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8%
Biochemistry, Genetics and Molecular Biology
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8%
Agricultural and Biological Sciences
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8%
Other
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Unknown
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33%
Attention Score in Context
Attention Score in Context
This research output has an Altmetric Attention Score of 6. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 02 February 2016.
All research outputs
#6,780,480
of 31,542,270 outputs
Outputs from Carbohydrate Research
#596
of 6,297 outputs
Outputs of similar age
#21,281
of 168,966 outputs
Outputs of similar age from Carbohydrate Research
#5
of 18 outputs
Altmetric has tracked 31,542,270 research outputs across all sources so far. This one has received more attention than most of these and is in the 74th percentile.
So far Altmetric has tracked 6,297 research outputs from this source. They receive a mean Attention Score of 3.7. This one has gotten more attention than average, scoring higher than 73% of its peers.
Older research outputs will score higher simply because they've had more time to accumulate mentions. To account for age we can compare this Altmetric Attention Score to the 168,966 tracked outputs that were published within six weeks on either side of this one in any source. This one has done well, scoring higher than 77% of its contemporaries.
We're also able to compare this research output to 18 others from the same source and published within six weeks on either side of this one. This one has gotten more attention than average, scoring higher than 50% of its contemporaries.
