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3 Biosynthesis of the Arabinogalactan-Peptidoglycan Complex of

Authors: Dean C. Crick1, Patrick J. Brennan2
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Affiliations: 1: Department of Microbiology, Immunology and Pathology, Colorado State University, Fort Collins, CO 80523; 2: Department of Microbiology, Immunology and Pathology, Colorado State University, Fort Collins, CO 80523
Content Type: Monograph
Publication Year: 2008
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Abstract:

Recent developments in genomics, bioinformatics, proteomics, and analytical techniques have resulted in a more detailed and thorough understanding of the structure of the mycobacterial cell wall core and its biosynthesis. Indeed, much of the current interest in its biosynthesis is driven by the need for novel, alternative drugs to counteract drug-resistant tuberculosis. The tetrapeptide side chains of peptidoglycan (PG) consist of L-alanyl-D-isoglutaminylmeso-diaminopimelyl-D-alanine (L-Ala-D-Glu-Apm- D-Ala), with the Glu and Apm being further amidated. Recent mass spectrometric analysis suggests that the arabinan chains released from the cell wall by an endogenous arabinase are also approximately 30 residues long and indicates that galactosamine (GalNH) residues in Arabinogalactan (AG) isolated from the CSU20 strain are found on the C2 position of some of the internal 3,5-branched residues. Many of the insights to understanding the biosynthesis of the cell wall core are derived from earlier structural analysis. In general, polyprenyl diphosphate (Pol-P-P) molecules are synthesized through sequential condensation of isopentenyl diphosphate (IPP, derived from methylerythritol phosphate in mycobacteria) with allylic diphosphates, reactions that are catalyzed by prenyl diphosphate synthases. Synthesis of AG begins with the formation of the linker unit, and then there appears to be a concomitant extension of the galactan and arabinan moieties. The structural complexity of mycobacterial arabinofuran present in AG is likely to be reflected in a complex biosynthetic pathway, and arabinosyl transferases are now being rapidly identified in spp.

Citation: C. Crick D, J. Brennan P. 2008. 3 Biosynthesis of the Arabinogalactan-Peptidoglycan Complex of , p 25-39. In Daffé M, Reyrat J, Avenir G (ed), The Mycobacterial Cell Envelope. ASM Press, Washington, DC. doi: 10.1128/9781555815783.ch3
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3 Biosynthesis of the Arabinogalactan-Peptidoglycan Complex of Mycobacterium tuberculosis
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Citation: C. Crick D, J. Brennan P. 2008. 3 Biosynthesis of the Arabinogalactan-Peptidoglycan Complex of , p 25-39. In Daffé M, Reyrat J, Avenir G (ed), The Mycobacterial Cell Envelope. ASM Press, Washington, DC. doi: 10.1128/9781555815783.ch3
/content/10.1128/9781555815783.ch03.ch03fig01
Figure 1.
Schematic diagram of the mycolyl-arabinogalactan-peptidoglycan complex of . The positions of the succinyl and -galactosamine residues are indicated ( ).
10.1128/9781555815783/f0026-01_thmb.gif
10.1128/9781555815783/f0026-01.gif
Image of Figure 1.
Figure 1.

Schematic diagram of the mycolyl-arabinogalactan-peptidoglycan complex of . The positions of the succinyl and -galactosamine residues are indicated ( ).

Citation: C. Crick D, J. Brennan P. 2008. 3 Biosynthesis of the Arabinogalactan-Peptidoglycan Complex of , p 25-39. In Daffé M, Reyrat J, Avenir G (ed), The Mycobacterial Cell Envelope. ASM Press, Washington, DC. doi: 10.1128/9781555815783.ch3
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/content/10.1128/9781555815783.ch03.ch03fig02
Figure 2.
Schematic diagram showing key intermediates in mycolyl-arabinogalactan-peptidoglycan complex synthesis and the central role played by decaprenyl phosphate.
10.1128/9781555815783/f0028-01_thmb.gif
10.1128/9781555815783/f0028-01.gif
Image of Figure 2.
Figure 2.

Schematic diagram showing key intermediates in mycolyl-arabinogalactan-peptidoglycan complex synthesis and the central role played by decaprenyl phosphate.

Citation: C. Crick D, J. Brennan P. 2008. 3 Biosynthesis of the Arabinogalactan-Peptidoglycan Complex of , p 25-39. In Daffé M, Reyrat J, Avenir G (ed), The Mycobacterial Cell Envelope. ASM Press, Washington, DC. doi: 10.1128/9781555815783.ch3
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Figure 3.
Pathways involved in the biosynthesis of decaprenyl phosphate and peptidoglycan with respect to the topology of the plasma membrane. A simple hypothetical scheme for decaprenyl phosphate recycling has been included; more complex possibilities exist, as is discussed in the text. Gene (Rv) numbers have been provided for enzymes from which have been biochemically demonstrated to catalyze the indicated reaction. Symbols used: , phosphate; , -acylmuramic acid; , -acetylglucosamine.
10.1128/9781555815783/f0029-01_thmb.gif
10.1128/9781555815783/f0029-01.gif
Image of Figure 3.
Figure 3.

Pathways involved in the biosynthesis of decaprenyl phosphate and peptidoglycan with respect to the topology of the plasma membrane. A simple hypothetical scheme for decaprenyl phosphate recycling has been included; more complex possibilities exist, as is discussed in the text. Gene (Rv) numbers have been provided for enzymes from which have been biochemically demonstrated to catalyze the indicated reaction. Symbols used: , phosphate; , -acylmuramic acid; , -acetylglucosamine.

Citation: C. Crick D, J. Brennan P. 2008. 3 Biosynthesis of the Arabinogalactan-Peptidoglycan Complex of , p 25-39. In Daffé M, Reyrat J, Avenir G (ed), The Mycobacterial Cell Envelope. ASM Press, Washington, DC. doi: 10.1128/9781555815783.ch3
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Figure 4.
Pathways involved in arabinogalactan synthesis showing the intersection of galactan synthesis and decaprenylphosphorylarabinose (DPA) synthesis. Gene (Rv) numbers have been provided for enzymes from which have been biochemically demonstrated to catalyze the indicated reaction ( ).
10.1128/9781555815783/f0030-01_thmb.gif
10.1128/9781555815783/f0030-01.gif
Image of Figure 4.
Figure 4.

Pathways involved in arabinogalactan synthesis showing the intersection of galactan synthesis and decaprenylphosphorylarabinose (DPA) synthesis. Gene (Rv) numbers have been provided for enzymes from which have been biochemically demonstrated to catalyze the indicated reaction ( ).

Citation: C. Crick D, J. Brennan P. 2008. 3 Biosynthesis of the Arabinogalactan-Peptidoglycan Complex of , p 25-39. In Daffé M, Reyrat J, Avenir G (ed), The Mycobacterial Cell Envelope. ASM Press, Washington, DC. doi: 10.1128/9781555815783.ch3
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