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d -Alanyl-lipoteichoic acid (d -alanyl-LTA) containsd -alanine ester residues which control the ability of this polyer to chelate Mg2+ . InLactobacillus casei a two-step in vitro reaction sequence catalyzed by thed -alanine-activating enzyme andd -alanine:membrane acceptor ligase incorporatesd -alanine into membrane acceptor. In this paper we provide additional evidence that the in vitro system catalyzes the covalent incorporation ofd -[14 C]alanine into membrane acceptor which is the poly([3 H]glycerol phosphate) moiety ofd -alanyl-LTA. This conclusion was supported by the observation that thed -[14 C]alanine and [3 H]glycerol labels of the partially purified product were co-precipitated by antiserum containing globulins specific for poly(glycerol phosphate). The isolation ofd -[14 C]alanyl-[3 H]glycerol fromd -[14 C]alanine·[3 H]glycerol-labeledd -alanyl-LTA synthesized in the in vitro system indicated that thed -alanine was linked to the poly(glycerol phosphate) chain of the LTA. A comparison of the reactivities of thed -alanine residues ofd -alanyl-glycerol andd -alanyl-LTA supported the conclusion that the incorporated residue ofd -alanine was attached by an ester linkage. Thus, the data indicated that the in vitro system catalyzes the incorporation ofd -alanine covalently linked by ester linkages to the glycerol moieties of the poly(glycerol phosphate) chains ofd -alanyl-LTA. New procedures are presented for the partial purification ofd -alanyl-LTA with a high yield of ester-linkedd -alanine and for the sequential degradation of the poly(glycerol phosphate) moiety substituted withd -alanine ofd -alanyl-LTA with phosphodiesterase II/phosphatase fromAspergillus niger .

Biosynthesis of d -Alanyl-Lipoteichoic Acid: Characterization of Ester-Linked d -Alanine in the In Vitro-Synthesized Product