Recent studies have demonstrated that the O-antigens of some pathogenic bacteria such as Brucella abortus, Francisella tularensis, and Campylobacter jejuni contain quite unusual N-formylated sugars (3-formamido-3,6-dideoxy-d-glucose or 4-formamido-4,6-dideoxy-d-glucose). Typically, four enzymes are required for the formation of such sugars: a thymidylyltransferase, a 4,6-dehydratase, a pyridoxal 5'-phosphate or PLP-dependent aminotransferase, and an N-formyltransferase. To date, there have been no published reports of N-formylated sugars associated with Mycobacterium tuberculosis. A recent investigation from our laboratories, however, has demonstrated that one gene product from M. tuberculosis, Rv3404c, functions as a sugar N-formyltransferase. Given that M. tuberculosis produces l-rhamnose, both a thymidylyltransferase (Rv0334) and a 4,6-dehydratase (Rv3464) required for its formation have been identified. Thus, there is one remaining enzyme needed for the production of an N-formylated sugar in M. tuberculosis, namely a PLP-dependent aminotransferase. Here we demonstrate that the M. tuberculosis rv3402c gene encodes such an enzyme. Our data prove that M. tuberculosis contains all of the enzymatic activities required for the formation of dTDP-4-formamido-4,6-dideoxy-d-glucose. Indeed, the rv3402c gene product likely contributes to virulence or persistence during infection, though its temporal expression and location remain to be determined. This article is protected by copyright. All rights reserved

6-dideoxy-d-glucose, Mycobacterium tuberculosis, aminotransferase, dTDP-4-amino-4, pyridoxal 5'-phosphate, Rv3402c

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10
5,0,0	aDQuip4N	96.2	73.0	69.8	58.1	66.8	18.0
5,0	P
5	P
	xXnucdT	86.2	39.8	72.2	86.5	66.6	?	?	?	138.5	?


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10
5,0,0	aDQuip4N	5.59	3.62	3.93	3.02	4.29	1.36
5,0	P
5	P
	xXnucdT	6.34	2.37	4.62	4.19	4.17	-	-	-	7.73	?


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9	C10/H10
5,0,0	aDQuip4N	96.2/5.59	73.0/3.62	69.8/3.93	58.1/3.02	66.8/4.29	18.0/1.36
5,0	P
5	P
	xXnucdT	86.2/6.34	39.8/2.37	72.2/4.62	86.5/4.19	66.6/4.17				138.5/7.73	?/?

The spectrum also has 4 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

Cc1cn([C@H]2C[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)O[C@H]3O[C@H](C)[C@@H](N)[C@H](O)[C@H]3O)O2)c(=O)[nH]c1=O

547.347 g/mol (C₁₆H₂₇N₃O₁₄P₂)