Penicillin 4-hydroxybenzyl

X-ray, 7, 300 <68MI51100, 76AX(B)2279) Penicillin, D-a-amino-p-hydroxybenzyl-(amoxicillin)... 

Amoxicillin — see Penicillin, D-n-amino-p-hydroxybenzyl-Amozonolysis cycloalkenes, 6, 876 Amphotericin B antifungal agent veterinary use, 1, 211... 

D-(-)-a-Amino-a-(4-hydroxyphenyl)acetamido]penicillanic acid and D-(-)-a-Amino-p-hydroxybenzyl penicillin. In some early literature amoxicillin was referred to as p-hydroxy ampicillin. 

Amoxicillin (uh-MOX-uh-sill-in) is also known as D-(-)-alpha-amino-p-hydroxybenzyl penicillin and (2S,5R,6R)-... 

The side-chain was found to be variable and to be dependent on the nature of precursors in the fermentation medium. Thus R was zl -pentenyl in penicillin F, benzyl in penicillin G, -hydroxybenzyl in penicillin X and M-heptyl in penicillin K. The different penicillins were then named according to the nature of the group R, penicillin G, for example, being called benzyl-penicillin. Several hundred biosynthetic penicillins, in which R-CO was derived from a mono-substituted acetic acid, were obtained from fermentations of Penicillium notatum or Penicillium chrysogenum in the presence of appropriate precursors. However, penicillins with side-chains derived from di-substituted acetic acids, or with highly polar side-chains, did not appear to be generally accessible by this route. 

From the I b the epi-6-APA (lllc), epi-Pen G (llld),72 g.nd epi—ampillicin (llle) have b een obtained. Compounds Illd and Ille show very low antibacterial activity in comparison to materials having the natural configuration at C-6. The 6-epi-penicillin V methyl ester has been synthesized. The aldol condensation of formaldehyde and benzaldehyde on carbon 6 In 6-APA has been studied,and the 6-hydroxybenzyl penicillin G synthesized from the latter showed only weak antibacterial activity. 

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