Uptake of unnatural trehalose analogs as a
reporter for Mycobacterium tuberculosis. Nat
Chem Biol 7:228–235
16. Kamariza M, Shieh P, Ealand CS, Peters JS,
Chu B, Rodriguez-Rivera FP, Babu Sait MR,
Treuren WV, Martinson N, Kalscheuer R, Kana
BD (2018) Rapid detection of Mycobacterium
tuberculosis in sputum with a solvatochromic
trehalose probe. Sci Transl Med 10(430):
eaam6310.
https://doi.org/10.1126/
scitranslmed.aam6310
17. Swarts BM, Holsclaw CM, Jewett JC, Alber M,
Fox DM, Siegrist MS, Leary JA, Kalscheuer R,
Bertozzi CR (2012) Probing the mycobacterial
trehalome with bioorthogonal chemistry. J Am
Chem Soc 134:16123–16126
18. Hodges HL, Brown RA, Crooks JA, Weibel
DB, Kiessling LL (2018) Imaging mycobacterial growth and division with a fluorogenic
probe. Proc Natl Acad Sci U S A
115:5271–5276
19. Holmes NJ, Kavunja HW, Yang Y, Vannest BD,
Ramsey CN, Gepford DM, Banahene N,
Poston AW, Piligian BF, Ronning DR, Oja
AK, Swarts BM (2019) A FRET-based fluorogenic trehalose dimycolate analogue for probing mycomembrane-remodeling enzymes of
mycobacteria. ACS Omega 4:4348–4359
20. Rostovtsev VV, Green LG, Fokin VV, Sharpless
KB (2002) A stepwise Huisgen cycloaddition
process: copper(I)-catalyzed Regioselective
“ligation” of Azides and terminal alkynes.
Angew Chem Int Ed 41:2596–2599
21. Agard NJ, Prescher JA, Bertozzi CR (2004) A
strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. J Am Chem Soc
126:15046–15047
22. Foley HN, Stewart JA, Kavunja HW, Rundell
SR, Swarts BM (2016) Bioorthogonal chemical reporters for selective in situ probing of
mycomembrane components in mycobacteria.
Angew Chem Int Ed 55:2053–2057
23. Kavunja HW, Piligian BF, Fiolek TJ, Foley HN,
Nathan TO, Swarts BM (2016) A chemical
reporter strategy for detecting and identifying
O-mycoloylated proteins in Corynebacterium.
Chem Commun 52:13795–13798
24. Fiolek TJ, Banahene N, Kavunja HW, Holmes
NJ, Rylski AK, Pohane AA, Siegrist MS, Swarts
BM (2019) Engineering the mycomembrane
of live mycobacteria with an expanded set of
trehalose monomycolate analogues. Chembiochem 20:1282–1291
25. Blackman ML, Royzen M, Fox JM (2009) The
Tetrazine ligation: fast bioconjugation based
on inverse- electron-demand Diels-Alder reactivity. J Am Chem Soc 130:13518–13519
26. Siegrist MS, Swarts BM, Fox DM, Lim SA,
Bertozzi CR (2015) Illumination of growth,
division and secretion by metabolic labeling of
the bacterial cell surface. FEMS Microbiol Rev
39:184–202
27. Patterson DM, Nazarova LA, Prescher JA
(2014) Finding the right (bioorthogonal)
chemistry. ACS Chem Biol 9:592–605
28. Rodriguez-Rivera FP, Zhou X, Theriot JA,
Bertozzi CR (2017) Visualization of mycobacterial membrane dynamics in live cells. J Am
Chem Soc 139:3488–3495
29. RF P, Xiaoxue Z, TJ A, BC R (2018) Acute
modulation of mycobacterial cell envelope biogenesis by front-line tuberculosis drugs.
Angew Chem Int Ed 57:5267–5272
30. Zhou X, Rodriguez-Rivera FP, Lim HC, Bell
JC, Bernhardt TG, Bertozzi CR, Theriot JA
(2019) Sequential assembly of the septal cell
envelope prior to V snapping in Corynebacterium glutamicum. Nat Chem Biol 15:221–231
31. Garcı ´a-Heredia A, Pohane AA, Melzer ES,
Carr CR, Fiolek TJ, Rundell SR, Lim HC,
Wagner JC, Morita YS, Swarts BM, Siegrist
MS (2018) Peptidoglycan precursor synthesis
along the sidewall of pole-growing mycobacteria. Elife 7:e37243. https://doi.org/10.
7554/eLife.37243
32. Pohane AA, Carr CR, Garhyan J, Swarts BM,
Siegrist MS. Trehalose recycling promotes
energy-efficient mycomembrane reorganization in nutrient-limited mycobacteria. bioRxiv.
2019. https://doi.org/10.1101/758177
33. Xu Z, Meshcheryakov VA, Poce G, Chng S-S
(2017) MmpL3 is the flippase for mycolic acids
in mycobacteria. Proc Natl Acad Sci U S A
114:7993–7998
34. Rundell SR, Wagar ZL, Meints LM, Olson CD,
O’Neill MK, Piligian BF, Poston AW, Hood
RJ, Woodruff PJ, Swarts BM (2016)
Deoxyfluoro-D-trehalose (FDTre) analogues
as potential PET probes for imaging mycobacterial
infection.
Org
Biomol
Chem
14:8598–8609
35. Pen ˜a-Zalbidea S, Huang AYT, Kavunja HW,
Salinas B, Desco M, Drake C, Woodruff PJ,
Vaguero JJ, Swarts BM (2019) Chemoenzymatic radiosynthesis of 2-deoxy-2-[18F]
fluoro-D-trehalose ([18F]-2-FDTre): a PET
radioprobe for in vivo tracing of trehalose
metabolism. Carbohydr Res 472:16–22
36. Dutta AK, Choudhary E, Wang X,
Za ´horszka M, Forbak M, Lohner P, Jessen
HJ, Agarwal N, Kordula ´kova ´ J, Jessen-Trefzer
Trehalose Probe Labeling
397
reporter for Mycobacterium tuberculosis. Nat
Chem Biol 7:228–235
16. Kamariza M, Shieh P, Ealand CS, Peters JS,
Chu B, Rodriguez-Rivera FP, Babu Sait MR,
Treuren WV, Martinson N, Kalscheuer R, Kana
BD (2018) Rapid detection of Mycobacterium
tuberculosis in sputum with a solvatochromic
trehalose probe. Sci Transl Med 10(430):
eaam6310.
https://doi.org/10.1126/
scitranslmed.aam6310
17. Swarts BM, Holsclaw CM, Jewett JC, Alber M,
Fox DM, Siegrist MS, Leary JA, Kalscheuer R,
Bertozzi CR (2012) Probing the mycobacterial
trehalome with bioorthogonal chemistry. J Am
Chem Soc 134:16123–16126
18. Hodges HL, Brown RA, Crooks JA, Weibel
DB, Kiessling LL (2018) Imaging mycobacterial growth and division with a fluorogenic
probe. Proc Natl Acad Sci U S A
115:5271–5276
19. Holmes NJ, Kavunja HW, Yang Y, Vannest BD,
Ramsey CN, Gepford DM, Banahene N,
Poston AW, Piligian BF, Ronning DR, Oja
AK, Swarts BM (2019) A FRET-based fluorogenic trehalose dimycolate analogue for probing mycomembrane-remodeling enzymes of
mycobacteria. ACS Omega 4:4348–4359
20. Rostovtsev VV, Green LG, Fokin VV, Sharpless
KB (2002) A stepwise Huisgen cycloaddition
process: copper(I)-catalyzed Regioselective
“ligation” of Azides and terminal alkynes.
Angew Chem Int Ed 41:2596–2599
21. Agard NJ, Prescher JA, Bertozzi CR (2004) A
strain-promoted [3 + 2] azide-alkyne cycloaddition for covalent modification of biomolecules in living systems. J Am Chem Soc
126:15046–15047
22. Foley HN, Stewart JA, Kavunja HW, Rundell
SR, Swarts BM (2016) Bioorthogonal chemical reporters for selective in situ probing of
mycomembrane components in mycobacteria.
Angew Chem Int Ed 55:2053–2057
23. Kavunja HW, Piligian BF, Fiolek TJ, Foley HN,
Nathan TO, Swarts BM (2016) A chemical
reporter strategy for detecting and identifying
O-mycoloylated proteins in Corynebacterium.
Chem Commun 52:13795–13798
24. Fiolek TJ, Banahene N, Kavunja HW, Holmes
NJ, Rylski AK, Pohane AA, Siegrist MS, Swarts
BM (2019) Engineering the mycomembrane
of live mycobacteria with an expanded set of
trehalose monomycolate analogues. Chembiochem 20:1282–1291
25. Blackman ML, Royzen M, Fox JM (2009) The
Tetrazine ligation: fast bioconjugation based
on inverse- electron-demand Diels-Alder reactivity. J Am Chem Soc 130:13518–13519
26. Siegrist MS, Swarts BM, Fox DM, Lim SA,
Bertozzi CR (2015) Illumination of growth,
division and secretion by metabolic labeling of
the bacterial cell surface. FEMS Microbiol Rev
39:184–202
27. Patterson DM, Nazarova LA, Prescher JA
(2014) Finding the right (bioorthogonal)
chemistry. ACS Chem Biol 9:592–605
28. Rodriguez-Rivera FP, Zhou X, Theriot JA,
Bertozzi CR (2017) Visualization of mycobacterial membrane dynamics in live cells. J Am
Chem Soc 139:3488–3495
29. RF P, Xiaoxue Z, TJ A, BC R (2018) Acute
modulation of mycobacterial cell envelope biogenesis by front-line tuberculosis drugs.
Angew Chem Int Ed 57:5267–5272
30. Zhou X, Rodriguez-Rivera FP, Lim HC, Bell
JC, Bernhardt TG, Bertozzi CR, Theriot JA
(2019) Sequential assembly of the septal cell
envelope prior to V snapping in Corynebacterium glutamicum. Nat Chem Biol 15:221–231
31. Garcı ´a-Heredia A, Pohane AA, Melzer ES,
Carr CR, Fiolek TJ, Rundell SR, Lim HC,
Wagner JC, Morita YS, Swarts BM, Siegrist
MS (2018) Peptidoglycan precursor synthesis
along the sidewall of pole-growing mycobacteria. Elife 7:e37243. https://doi.org/10.
7554/eLife.37243
32. Pohane AA, Carr CR, Garhyan J, Swarts BM,
Siegrist MS. Trehalose recycling promotes
energy-efficient mycomembrane reorganization in nutrient-limited mycobacteria. bioRxiv.
2019. https://doi.org/10.1101/758177
33. Xu Z, Meshcheryakov VA, Poce G, Chng S-S
(2017) MmpL3 is the flippase for mycolic acids
in mycobacteria. Proc Natl Acad Sci U S A
114:7993–7998
34. Rundell SR, Wagar ZL, Meints LM, Olson CD,
O’Neill MK, Piligian BF, Poston AW, Hood
RJ, Woodruff PJ, Swarts BM (2016)
Deoxyfluoro-D-trehalose (FDTre) analogues
as potential PET probes for imaging mycobacterial
infection.
Org
Biomol
Chem
14:8598–8609
35. Pen ˜a-Zalbidea S, Huang AYT, Kavunja HW,
Salinas B, Desco M, Drake C, Woodruff PJ,
Vaguero JJ, Swarts BM (2019) Chemoenzymatic radiosynthesis of 2-deoxy-2-[18F]
fluoro-D-trehalose ([18F]-2-FDTre): a PET
radioprobe for in vivo tracing of trehalose
metabolism. Carbohydr Res 472:16–22
36. Dutta AK, Choudhary E, Wang X,
Za ´horszka M, Forbak M, Lohner P, Jessen
HJ, Agarwal N, Kordula ´kova ´ J, Jessen-Trefzer
Trehalose Probe Labeling
397