Table 3.

Selected chemical reporters for bacterial glycoproteins

Target	Metabolite	Compound	Reporter group (X)	Bioorthogonal reaction(s)	Proposed route	Speciesa	Applicationsb	Synthesis	Notesa	Refc
Flagellin pseudaminic acid	AltdiNAc	AltNAc4NAz 75 (Fig. 27)	Azide	Staudinger ligation	Intracellular	C. jejuni (GN)	Detection of labeled flagellin	Chemo-enzymatic	Labeled flagellin but no other proteins in C. jejuni	202
Flagellin legionaminic acid	MandiNAc	83 (Fig. 28)	Azide	SPAAC	Intracellular	C. jejuni (GN)	Detection of labeled flagellin; in vitro imaging; identification of GTase	Chemical	Labeled flagellin but no other proteins in C. jejuni; peracetylation abolished labeling	193
Glycoproteins	GlcNAc	Ac4GlcNAz 86 (Fig. 29)	Azide	Staudinger ligation	Intracellular	H. pylori (GN)	Detection and profiling of labeled proteins; identification of GTases; delivery of immune modulator	Chemical; comm. available	Peracetylation required for labeling; no information available about glycan structure; did not incorporate into a variety of other bacterial species	215
	Bac	Ac2Bac-DiNAz 88 (Fig. 29)	Azide	Staudinger ligation	Intracellulard	H. pylori (GN), C. jejuni (GN), R. solanacearum (GN), B. thailandensis (GN)	Detection of labeled proteins	Chemical	Peracetylated reporter labeled bacteria, unacetylated version not tested	216
	DATDG	Ac2DATDG-DiNAz 89 (Fig. 29)	Azide	Staudinger ligation	Intracellulard	H. pylori (GN), C. jejuni (GN), R. solanacearum (GN)	Detection of labeled proteins	Chemical	Peracetylated reporter labeled bacteria, unacetylated version not tested	216
	L-fucose	FucAl 59 (Fig. 21)	Alkyne	CuAAC	Intracellular	B. fragilis (GN), P. distasons (GN)	Detection of labeled proteins	Chemical		217

^aGram classification: GN, Gram-negative; GP, Gram-positive; M, mycobacteria.

^bIn vitro refers to bacterial labeling experiments performed in broth culture; in vivo refers to bacterial labeling experiments performed in a host cell or organism.

^cInitial publication(s) referenced. See text for references for follow-up studies and applications.

^dLimited evidence available to support proposed route of incorporation and/or identity of labeled target (see text).