Issue in Honor of Prof. Atta-ur-Rahman ARKIVOC 2007 (vii) 241-253
L-Pro D-Pro D-allo-Thr tripropeptins
n component
NH
6 ZCH3 7 A
N H
H2N
8 B 9 C 10 D 11 E
nCH3NH(R) (R) OHH3C ON (R) O N(S) NH O (S) NHO (R) (R) HO OHN (S) OOL-Arg HO (S)OHCOOH N N H (S) (S) OOO OH (S) (R) H H HCOOH L-threo-hydroxy-Asp
D-threo-hydroxy-Asp trans-3-hydroxy-L-Pro
L-Ser
Figure 1. Structure of TPPs.
They show potent antimicrobial activities against gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA), vancomycin-resistant Enterococcus spp. and penicillin-resistant Streptococcus pneumoniae. Their antimicrobial activities are well proportioned to the length of fatty acyl chain up to C-16 (Table 1).2
Table 1. Antimicrobial activities of TPPs and related compounds against MSSA and MRSA
test sample MIC (µg/ml) MIC (µg/ml)
MSSA (10 strains) MRSA (10 strains)
range MIC50 MIC90 range MIC50 MIC90 tripropeptin A(C-13) 3.13-12.5 6.25 6.25 0.78-12.5 6.25 12.5 tripropeptin B (C-14) 0.78-3.13 1.56 3.13 0.39-3.13 3.13 3.13 tripropeptin C (C-15) 0.39-0.78 0.78 0.78 0.78 0.78 1.56 tripropeptin D (C-16 0.39-0.78 0.78 0.78 0.78 0.78 0.78 tripropeptin E (C-17) 0.39-0.78 0.78 0.78 0.78 0.78 1.56 tripropeptin Z (C-12) 12.5-50 50 50 50 50 100 vancomycin 0.78 0.78 0.78 0.39-1.56 1.56 1.56 teicoplanin 0.39-0.78 0.39 0.78 0.20-1.56 0.78 1.56 meropenem 0.05-0.10 0.10 0.10 6.25-50 12.5 50 levofloxacin 0.05-0.39 0.10 0.20 3.13-100 25 >100 ofloxacin 0.20-0.78 0.39 0.39 6.25-100 100 >100 ampicillin 0.10-3.13 0.78 3.13 6.25-50 25 50 arbekacin 0.20-0.78 0.39 0.78 0.20-0.39 0.39 0.39 erythromycin 0.10-100 0.20 12.5 >100 >100 >100 tetracycline 0.20 0.20 0.20 1.56-50 50 50 fosfomycin 3.13-50 6.25 25 >100 >100 >100
Mueller Hinton agar (Difco) 37 ºC, 18 h
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