Please indicate how water might hydrogen bond with D-Ala-D-Lac excluding the terminal amine and terminal carboxylic acid H₂N CH₂ CH₂ OH

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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Please indicate how water might hydrogen bond with D-Ala-D-Lac excluding the terminal amine
and terminal carboxylic acid
H₂N
CH₂
HO
H
HO₂C
This change in hydrogen bonding pattern is all the bacteria needs to survive. Interestingly
changing an oxygen in vancomycin aglycone (compound 5 below) to an NH (compound 6
below) restores activity against VRE, strains with D-Ala-D-Lac, and compound 6 is still active
against strains with (D-Ala-D-Ala). Why?
HO
NH
N
CH₂
HH
OH
OH
OH
OH
H₂N-
OH
5, Y = O
6, Y = NH
7, Y = H₂
8, Y=S
NHMe
MICa
compd (ug/mL)
640
0.31
31
>640
5
6
7
8
aVanA VRE
Transcribed Image Text:Please indicate how water might hydrogen bond with D-Ala-D-Lac excluding the terminal amine and terminal carboxylic acid H₂N CH₂ HO H HO₂C This change in hydrogen bonding pattern is all the bacteria needs to survive. Interestingly changing an oxygen in vancomycin aglycone (compound 5 below) to an NH (compound 6 below) restores activity against VRE, strains with D-Ala-D-Lac, and compound 6 is still active against strains with (D-Ala-D-Ala). Why? HO NH N CH₂ HH OH OH OH OH H₂N- OH 5, Y = O 6, Y = NH 7, Y = H₂ 8, Y=S NHMe MICa compd (ug/mL) 640 0.31 31 >640 5 6 7 8 aVanA VRE
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