The aminocyclitols are compounds related to
cyclitols . They possess features of relative and absolute configuration that are characteristic of their class and have been extensively studied; but these features are not clearly displayed by general methods of stereochemical nomenclature, so that special methods of specifying their configuration are justified and have long been used. In other than stereochemical respects, their nomenclature should follow the general rules of
organic chemistry .
[1]
Aminocyclitol natural products
The aminocyclitol family of
natural products is a class of sugar-derived microbial
secondary metabolites that demonstrate significant biological activities. Aminocyclitols are found as a component of
aminoglycoside
antibiotics which is also called as pseudosugars or pseudosaccharides. Aminocyclitols have chemical structures of a carbon ring with
amine
functional group (s). The class of aminocyclitol containing natural products can be divided by ring sizes or types of precursors.
Five-membered ring aminocyclitols
pactamycin
Six-membered ring aminocyclitols
2-deoxy-scyllo -inosose derived aminoglycosides
This class includes
kanamycin ,
neomycin ,
gentamicin ,
apramycin ,
hygromycin .
myo -inositol 1-phosphate derived aminoglycosides
This class includes
streptomycin ,
spectinomycin .
sedoheptulose 7-phosphate derived C7N aminocyclitol natural products
This class includes
acarbose ,
validamycin , validoxylamine A,
[2] salbostatin,
cetoniacytone A ,
[3] pyralomicin 1a,
[4] kirkamide
[5]
Biosynthesis of C7N aminocyclitols
Sedoheptulose 7-phosphate , a
pentose phosphate pathway intermediate, is a common precursor of C7N aminocyclitol moiety of natural products, such as
acarbose ,
[6]
validamycin A,
[7] salbostatin,
[8] cetoniacytone A,
[9]
[10] and pyralomicin 1a.
[11] 2-epi-5-epi-valiolone synthase (EEVS),
[6]
[12]
[13] one of the sugar phosphate cyclase family enzyme
[9] and which is a homolog of
3-dehydroquinate synthase in
shikimate pathway , catalyzes the formation of a common intermediate, 2-epi-5-epi-valiolone from
sedoheptulose 7-phosphate . After multiple enzyme reaction steps, which include
phosphorylation ,
[14]
[15]
epimerization ,
[16]
dehydration , and keto-reduction reactions,
valienol , an important core structure is formed which leads to the formation of C7N aminocyclitol containing natural products. In
validamycin biosynthesis, the C-N linkage which connect the C7 cyclitol moiety to the other was found to be formed by unprecedented actions of
nucleotidyltransferase
[17] and
glycosyltransferase -like enzymes
[18]
[19]
[20] (which is termed pseudoglycosyltransferase).
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