By N. H. Georgopapadakou, R. B. Sykes (auth.), Professor Dr. Arnold L. Demain, Ms. Nadine A. Solomon (eds.)

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Additional resources for Antibiotics: Containing the Beta-Lactam Structure, Part II

Example text

9). The similarity of the endopeptidase to oo-carboxypeptidase reaction is evident since IX to the susceptible peptide bond is a free carboxyl group on the o-symmetric center of diaminopimelic acid (R4 = OR in Fig. 9). Depending on the nature of nucleophilic acceptor, oD-carboxypeptidase-associated transpeptidase activity can be divided into two types: (1) acceptor is hydroxylamine, glycine or another amino acid and probably binds at the donor site (transpeptidation is reversed hydrolysis); (2) acceptor is GlY-L-Ala or another peptide and binds at a site topologically distinct from the donor site (natural model transpeptidation).

I981a) COYETTE et al. (1977), GEORGOPAPADAKOU and LIU unpublished work KOZARICH and STROMINGER (1978) McARTHUR and REYNOLDS (1979a, b, 1980) MARQUET et al. (1976) , Numbers in parentheses refer to corresponding molecular weights given in Tables 3 and 4 b Abbreviations: AGDAA, L-Ala-D-Glu-Meso-Dap-D-Ala-D-Ala; DLAA, Diac-L-Lys-D-Ala-D-Ala; UDPMAGDAA, UPDMurNAc-L-Ala-D-Glu-Meso-Dap-D-Ala-D-Ala; UDPMAGLAA, UPDMurNAc-L-Ala-D-Glu-L-Lys-D-Ala-D-Ala 45(39) B. megaterium - membrane tp N '-0 rJ> o· 5' 5- - > g.

Coli is highly sensitive to penicillin which releases slowly (half-life: 90 min at 37 0q, probably as penicilloic acid. In addition to carboxypeptidase activity (substrate: UDP-MurNAc-L-Ala-l'-D-Glu-meso-Dap-DAla-D-Ala) the enzyme also has natural model transeptidase activity (substrate: LAla-Y-D-Glu-meso-Dap-D-Ala-D-Ala), forming cross-linked tetrapeptide dimers (NGUYEN-DISTECHE et al. 1974a). p-Chloromercuribenzoate (2 mM) does not inhibit peptidase activity suggesting that a sulfhydryl group is not involved.

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