Gene/Protein
Disease
Symptom
Drug
Enzyme
Compound
Pivot Concepts:
Gene/Protein
Disease
Symptom
Drug
Enzyme
Compound
Target Concepts:
Gene/Protein
Disease
Symptom
Drug
Enzyme
Compound
Query: EC:2.3.1.107 (
DAT
)
1,471
document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)
The first asymmetric total synthesis of three structures proposed for mycobacterial diacyl trehaloses,
DAT
1
,
DAT
2
, and
DAT
3
is reported. The presence of two of these glycolipids,
DAT
1
and
DAT
3
, within different strains of pathogenic M. tuberculosis was confirmed, and it was shown that their abundance varies significantly. In mass spectrometry, synthetic
DAT
2
possessed almost identical fragmentation patterns to presumptive
DAT
2
from
Mycobacterium tuberculosis
H37Rv, but did not coelute by HPLC, raising questions as the precise relationship of the synthetic and natural materials. The synthetic DATs were examined as agonists for signaling by the C-type lectin,
Mincle
. The small differences in the chemical structure of the lipidic parts of
DAT
1
,
DAT
2
, and
DAT
3
led to drastic differences of
Mincle
binding and activation, with
DAT
3
showing similar potency as the known
Mincle
agonist trehalose dimycolate (TDM). In the future,
DAT
3
could serve as basis for the design of vaccine adjuvants with simplified chemical structure.
...
PMID:Asymmetric Total Synthesis of Mycobacterial Diacyl Trehaloses Demonstrates a Role for Lipid Structure in Immunogenicity. 3229 64
