Biomedical Engineering Reference
In-Depth Information
III-subclass-succinoyl trehalose lipids
OH
O
RO
XO
RO
OH
OX
O
OH
O
OH
OH
O
RO
RO
RO
OH
OX
O
OH
O
O
OH
CH
3
(CH
2
)
n
R=
n
= 6-14
O
X=
COOH
FIGURE 8.1 (continued)
Chemical structure of the family of basic trehalose lipids.
time isolated in 1959 by Middlebrook et al. (1959) the chemical structure of these
trehalose sulfolipids was not clarified until 1976 when Goren et al. characterized them
as 2,3,6,6′-tetraesters of trehalose 2′-sulfate. After purification and detailed analytical
characterization of glycolipids isolated from
Mycobacterium tuberculosis
, Domenech
et al. (2004) offered another structure in contrast with the structures proposed by
Goren et al. (1976) and Converse et al. (2003). The suggested chemical structure of
these glycolipids is 2,3-diacyl-d-trehalose-2′-sulfates (Figure 8.1. II-subclass).
C
hemiCal
s
truCtures
of
G
lyColiPiDs
P
roDuCeD
from
r
hodococcus
In terms of chemical structure, a lot of research was focused particularly in the
Rhodococcus
genus and trehalose-containing glycolipids, which often occur as a
complex mixture during the growth of rhodococci on
n
-alkanes, have been extensively
studied. Thus, Kretschmer et al. (1982) detected trehalose-6-monocorynemycolates,
trehalose-6,6′-diacylates (3-oxo-2-alkyl alkanoyc acid), and trehalose-6-acylates
(3-oxo-2-alkyl alkanoic acid) in the organic extract of
Rhodococcus erythropolis
DSM 43215 grown on
n
-alkanes. The major glycolipid species isolated from
Rhodococcus
strain H13-A was identified as 2.3.4.6,2′,3′,4′,6′-octa-acyltrehalose
and was acylated with C10-C22 saturated and unsaturated fatty acids, C35-C40
mycolic acids, hexanedioic, dodecanedioic acids, and 10-methyl hexadecanoic
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