• Embed Doc
  • Copy Link
  • Readcast
  • Collections
  • CommentGo Back
Download
 
 
Synthesis and antimicrobial activities of 3-
O
-Methyl-(
 R
)-1,2-
O
-trichloroethylidene-
α
-D-
 xylo
-furanuronic acid and 3-
O
-Methyl-(
 S 
)-1,2-
O
-trichloroethylidene-
α
-D-
 xylo
-furanuronic acid
Nilgün YEN
İ
L
a*
, Mustafa OSKAY
b
, Selda KUZU
a
, Emriye AY
a
, Kadir AY
a
 
a
Department of Chemistry, Sciences and Arts Faculty, Celal Bayar University, Manisa 45030, Turkey.
 b
Department of Biology, Sciences and Arts Faculty, Celal Bayar University, Manisa 45030, Turkey.
 __________________________________________________________________________________ 
 _ 
 __ Abstract:
The preparation of 3-
O
-methyl-1,2-
O
-(
S 
)-trichloroethylidene-
α
-
D
-
 xylo
-furanuronic acid and 3-
O
-methyl-1,2-
O
-(
 R
)-trichloroethylidene-
α
-
D
-
 xylo
-furanuronic acid starting from
β
-chloralose and
α
-chloralose are described. All new products were characterized by
1
H NMR,
13
C NMR and FTIR.Antibacterial potency of the product (
6b
) was determined in term of inhibition zone diameter and resultsshowed that this compound showed moderate activity against the tested microorganisms with inhibitionzones ranging from 10 to 22 mm. 
Keywords:
Antimicrobial activity; uronic acid; trichloroethylidene acetals;
β
-chloralose;
α
-chloralose _______________________________________________________________________________ 
 ___ 
 _ 
 __ 
1. Introduction
It has been proved that carbohydrates and their derivatives are used in therapeutic strategies for the treatment of cancer, AIDS and diabetes
1
. It is also known that trichloroethylidene acetals of sugars, existed as protecting groups, are potentially active derivatives of carbohydrates such as
α
-chloralose, used as a hypnotic drug and anaesthetic surgeries in laboratory works
2
. But,
β
-chloralose (the monoacetal derivative which trichloromethyl group is in
exo
-position) is toxiccompound
3
.In the last years, uronic acids, transformed their primary hydroxyl groups into a carboxylgroup because of oxidation, are generally applied to monosaccaharides
4
. The structures of uronicacids have been both aldehyde and carboxyl groups. They have received much attention becauseof their biological activities. Uronic acids and their derivatives are of quite important inmedicine, pharmacology and industrial area
5,6,7
. For example; glycosaminoglycans, carboxylic
*
Correspondence author:
Fax: +90 (236) 241 2158; E-mail:nilgun.yenil@bayar.edu.tr  
1
 
[c014]
 
acid formations on the sugar skeletons, play a key role in biomedical processes including growthfactor interactions, virus entry and angiogenesis
8,9
.Only a small proportion of pharmaceuticals derived from different sources have yet beenexamined for biologically active compounds, there is still enormous potential for theidentification of many novel agents. In addition, almost all antibiotics used today are of microbial origin. In medicine, we experience an increasing problem with pathogenic microbesthat becomes resistant to the most commonly used antibiotics.Therefore, the study reportedherein was undertaken to determine the preparation and the synthesis of a new series of 
uronicacids
derived from
β
-chloralose and
α
-chloralose as well as antimicrobial potency of them.
2. Results and
d
iscussion2.1. Chemistry
 In the present study, glucuronic acid derivatives have been synthesized from
α
-chloralose (
1a
)and
β
-chloralose (
1b
) as starting sugars. The corresponding reactions can be representedaccording to the synthetic protocol outlined in
Scheme 1
.
OOORR
1
OHOHOH
OOORR
1
OHOOCH
3
CH
3
2,2-DMP, PTSA, DMF
1a, 1b 2a, 2b
 
α
-chloralose: R=CCl
3
,
 
R 
1
=H
(1a)
 
β
-chloralose: R 
1
=CCl
3
,
 
R=H
(1b)
 
OOORR
1
OHOOCH
3
CH
3
CH
3
I, Ag
2
O, DMF
OOORR
1
OMeOOCH
3
CH
3
 
3a, 3b
 2
 
OOORR
1
OMeOOCH
3
CH
3
OOORR
1
OMeOHOH
1N HCl, 70°C
4a, 4b
 
OOORR
1
OMeOHOH
NaIO
4
MeOH, RT
OOORR
1
OMeOH
 5a, 5b
OOORR
1
OMeOH
HNO
3
, RT
OOORR
1
OMeOOH
 
6a, 6b
 
Scheme 1.
Synthetic pathway
for prepared compounds
 
The molecular structure of uronic acid derivatives (
6a
,
6b
) has been confirmed by usingspectral methods as a FT-IR,
1
H-NMR,
13
C-NMR.In FT-IR spectrums of 3-
O
-methyl-1,2-
O
-(
 R
)-trichloroethylidene-
α
-
D
-
 xylo
-furanuronicacid (
6a
) and 3-
O
-methyl-1,2-
O
-(
S 
)-trichloroethylidene-
α
-
D
-xylo-furanuronic acid (
6b
), thehydroxyl absorption bands of carboxylic acid groups of them was observed at 3514 cm
-1
and3415 cm
-1
, respectively. In regions 3015-2940 cm
-1 
and 3008-2834 cm
-1
, the C-H bonds wasappeared by some absorption bands. The absorption band of carbonyl bond (C=O) was alsosigned in region 1697 cm
-1
 and 1708 cm
-1
 (acid form), 1736 cm
-1
 (aldehyde form), respectively(
Table 1
). In the light of these IR data, it seems that the oxidation reaction of aldehyde groups of 
5a
and
5b
can easily be done. However, the spectral results of NMR proved that the oxidationreaction of compound
5a
was not completed while comparing with the oxidation of compound
5b
. It is also to note that there is the aldehyde form, approximately 30% yield, in the mixture asremaining, after the oxidation of 
5a
.
1
H NMR spectral data of compound
6a
and
6b
are given in
 
3
of 00

Leave a Comment

You must be to leave a comment.
Submit
Characters: ...
You must be to leave a comment.
Submit
Characters: ...