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ELSEVIER
Abstract
The two-dimensional representation of the cyclic carbohydrate structures, furanose and pyranose, and the anomeric designations
are described. Methods are represented to convert Fischer projection formulae, and both vertical and horizontal zig-zag representations to cyclic forms. 1998 IUBMB. Published by Elsevier Science Ltd. All rights reserved.
I. Introduction
Hm,,,-~:,,~1 OH
HD,-- ,~,-,~OH
3 HOD--~-,qlH
6 CH20H
O_
HO---C-.,H I
,OH I';II ~
3
OH
CH20H
(OH
OH
A S CH20H
HD" ~ .-,~mOH
0 HOmm,,-~.,,qUH
L~..
C.,emH
,
H D,-(~ .,~OH
:
-C-I>
HO
~ 1
5 H ==,-C -,91" ~ J
CH20H
"--OH
OH
'~-I
I
~OH HJ~OH
OH
-'-OH
H HO
I H OH
H -- C -- OH
H--C--OIl OH
CH20H
OH
OH
CH20H
CH20H
H).
0307-4412/98/$19.00 + 0.00 1998 IUBMB. Published by Elsevier Science Ltd. All rights reserved.
PII: S 0 3 0 7 - 4 4 1 2 ( 9 8 ) 0 0 0 8 2 - X
206
'1
H-C -OH
I
H--C--OH
I
HO--C--H
H-~I - O H
I
0
H-C--OH
HOCH 2 -
HO - C-- H
-O_H
HOOC - C -- OH
I
~H2
HO--C--H
I
I
H--C --OH
I
CH 2
0 H--C --OH
H--C--OH
I
I H-C--OH
I
C--H
H-C
HO--C--H
HO--C --H
I
H--C
'
I
CH20H
H-C--OH
I -
CH3
CH20H
Act
BB
C,,
D ,',
HD,-- C ".~1 OH
H m=.,.-C -~IOH',
a
i
H==,..-C;...,~ OH
,,
Hm,,.. C .-,~OH
i
=
3 HO m=,,- C - ~ I H
4
HO m=,..-C - ~ m H
J
H I=," C; - , ~ OH
I
I
HO--C--H
I
HO--C--H
I
H ~t~.,qmO
Hm=,-- ..~mOH ,:
H--C--H
- - I
OH
,4
6"
OH
~H2
H--C--OH
I
H2N-- C-- H
H--C--OH
I
H,-,
~N--C -- H
.~C-H
H--C--X
I
i
H--C--OH 9
H--C--OH r
z~OH
~H2
6 CH20H
HOOC--C-OH
"Nl~ i/
OH /
HOOC-- C-- OH
CH20H
I
I
HO--C--H
I
HO--C--H
I
H--C--OH
~ H2
HO--C--H
H--C--OH
HO--C--H
H2NX ~ / ~ O ' ~ o O H
0
",1___./OH
OH
CIH2OH J
207
3. Mills structures
208
0
4
I
2
H
a-D
or
<-7 (05
, 8 - D or u - L
Fig. 5. Anomericdesignation in cyclicstructures.The numberingshown
refers to an aldose; for a ketose, numbering starts at 2 at the anomeric
position. The drawings show Haworth structures; to obtain Mills structures replace the 'down' OH in the top drawings with a dashed bond
and OH to the side and the 'up' OH in the bottom drawings with a
wedge bond and OH to the side.
HO
HO
HO
H
.o. _OH
OH
H
0
HO----~k
OH
14" ~
~
"" r , OH OH
(31-1
C \
HO
'~OH
OH
OH
OH
H%
DOH
OH
- OH
'
HO
~''"
E
/o.
.o......o.
'
HOtZ~,,,~,~3/~.OH
J
OH
C
,,
5"~
~
OH
,o jc .,jo,
OH
.o
""
209
?HzOH
cH2
0
~4
C2
C6
HO"
"'OH
F
H-IC5-~.1
H04#~----"
bH
G
HO~W'~
NO~
"OH
OH
OH
H
Fig. 6. Transformation of a vertical zig zag projection to cyclic structures. Drawings refer to D-glucose, A, with specific operations
described in the text. Anomeric assignment could also be done more
simply on the basis of the Haworth structure, H, or Mills structures F or
G (but not E which has counterclockwise numbering). The 'down'
anomeric OH group for D-glucose, indicates the anomer (Fig. 5).
6 CIH20H
HO-C-H
X
A
x = ~,- . 1OH
OH 5 H
, / 0. \I .l 0
O,
O'"H
"'R
R~
H(~
---R
R=="~O"~
~'OH
6 CH20H
I "o OH
OH
R= CH20H (lot 6)
210
We are long past the time when Fischer had to represent stereochemistry within the confines of 19th century
printing techniques and without knowledge of actual
(absolute) configurations. As we a p p r o a c h the 21st
century, should we not consider a b a n d o n m e n t of the
long revered Fischer projections and H a w o r t h structures? They have served their p u r p o s e nobly, but "times
they are a'changin'" [9]. With the aid of computers,
linear m o n o s a c c h a r i d e s can be easily and accurately
r e p r e s e n t e d by vertical or horizontal zig zag projections,
and cyclic forms by Mills structures; although not
discussed here, conformational representations can also
be used in m a n y cases. A text of organic chemistry has
taken a small step in this direction using horizontal zig
zag projections for a brief description of glycolysis (but
without specifying the stereochemistry) and for reactions
of the tricarboxylic acid cycle [10]. An opportunity exists
for a text of biochemistry/molecular biology in which
furanose and pyranose structures would be in the same
style as those used for other cyclic materials, and linear
materials (e.g. a m i n o acids, carbohydrates, fatty acids)
would be in zig zag projections in h a r m o n y with those
often used for terpenes. With no disrespect for Haworth,
it can also be argued plausibly that Mills representations
References