21. Shui G, Bendt AK, Pethe K et al (2007) Sensitive profiling of chemically diverse bioactive
lipids. J Lipid Res 48:1976–1984
22. Hsu FF, Soehl K, Turk J et al (2011) Characterization of mycolic acids from the pathogen
Rhodococcus equi by tandem mass spectrometry
with electrospray ionization. Anal Biochem
409:112–122
23. Daffe ´ M, Lane ´elle MA, Puzo G (1983) Structural elucidation by field desorption and
electron-impact mass spectrometry of the
C-mycosides isolated from Mycobacterium
smegmatis.
Biochim
Biophys
Acta
751:439–443
24. Lopez-Marin LM, Prome ´ D, Lane ´elle MA et al
(1992) Fast-atom bombardment mass spectrometry of mycobacterial glycopeptidolipid
antigens: structural characterization by charge
remote fragmentation. J Am Soc Mass Spectrom 3:656–661
25. Lopez-Marin LM, Lane ´elle MA, Prome ´ D et al
(1992) Structure of a novel sulfate-containing
mycobacterial
glycolipid.
Biochemistry
31:11106–11111
26. Hsu FF, Pacheco S, Turk J et al (2012) Structural determination of glycopeptidolipids of
Mycobacterium smegmatis by high resolution
multiple-stage linear ion-trap mass spectrometry with electrospray ionization. J Mass Spectrom 47:1269–1281
27. Gilleron M, Quesniaux VFJ, Puzo G (2003)
Acylation state of the phosphatidylinositol hexamannosides from Mycobacterium bovis BCG
and Mycobacterium tuberculosis H37Rv and its
implication in toll-like receptor response. J Biol
Chem 278:29880–29889
28. Gilleron M, Lindner B, Puzo G (2006)
MS/MS approach for characterization of the
fatty acid distribution on mycobacterial phosphatidyl-myo-inositol mannosides. Anal Chem
78:8543–8548
29. Layre E, Gala-De Paepe D, Larrouy-Maumus
G et al (2011) Deciphering sulfoglycolipids of
Mycobacterium tuberculosis. J Lipid Res
52:1098–1110
30. Hsu FF, Turk J (2004) Studies on sulfatides by
quadrupole ion-trap mass spectrometry with
electrospray ionization: structural characterization and the fragment processes that include an
unusual internal galactose residue loss and the
classical charge remote fragmentation. J Am
Soc Mass Spectrom 15:536–546
31. Rhoades RR, Streeter C, Turk J et al (2011)
Characterization of sulfolipids of Mycobacterium tuberculosis H37Rv by multiple-stage linear ion trap high resolution mass spectrometry
with electrospray ionization reveals that family
of sulfolipid II predominates. Biochemistry
50:9135–9147
32. Camacho LR, Constant P, Raynaud C et al
(2001) Analysis of the phthiocerol dimycocerosate locus of Mycobacterium tuberculosis: evidence that this lipid is involved in the cell wall
permeability
barrier.
J
Biol
Chem
276:19845–19854
33. Constant P, Perez E, Malaga W et al (2002)
Role of the pks15/1 gene in the biosynthesis of
phenolglycolipids in the Mycobacterium tuberculosis
complex.
J
Biol
Chem
277:38148–38158
34. Fujita Y, Naka T, Doi T et al (2005a) Direct
molecular mass determination of trehalose
monomycolates from 11 species of mycobacteria by MALDI-TOF mass spectrometry.
Microbiology 151:1443–1425
35. Fujita Y, Naka T, McNeil MR et al (2005b)
Intact molecular characterization of cord factor
(trehalose 6,6
0 -dimycolatee) from nine species
of mycobacteria by MALDI-TOF mass spectrometry. Microbiology 151:3403–3416
36. Hsu FF, Wohlmann J, Turk J et al (2012)
Structural
definition
of
trehalose
6-monomycolates
and
trehalose
6,60 -dimycolates from the pathogen Rhodococcus
equi by multiple-stage linear ion-trap mass
spectrometry with electrospray ionization. J
Am Soc Mass Spectrom 22:2160–2170
37. Asselineau C, Tocanne G, Tocanne JF (1970)
Ste ´re ´ochimie des acides mycoliques. Bull Soc
Chim Fr 4:1455–1459
38. Rafidinarivo E, Prome ´ JC, Le ´vy-Fre ´bault V
(1985) New kinds of unsaturated mycolic
acids from Mycobacterium fallax sp. nov.
Chem Phys Lipids 36:215–228
39. Lacave C, Lane ´elle MA, Daffe ´ et al (1987)
Structure and metabolic study of the mycolic
acids of Mycobacterium fortuitum. Eur J Biochem 163:369–378
40. Lane ´elle MA, Lacave C, Daffe ´ M et al (1988)
Mycolic acids of Mycobacterium aurum. Structure and biogenetic implications. Eur J Biochem 177:631–635
41. Lane ´elle MA, Lacave C, Daffe ´ M et al (1989)
Mycolic acid metabolic filiation and location in
Mycobacterium aurum and Mycobacterium
phlei. Eur J Biochem 181:459–466
42. Daffe ´ M, Lane ´elle MA, Lacave C (1991) Structure and stereochemistry of mycolic acids of
Mycobacterium marinum and Mycobacterium
ulcerans. Res Microbiol 142:397–403
43. Tahiri N, Fodran P, Jayaraman D, Buter J et al
(2020) Total synthesis of a mycolic acid from
Mycobacterium tuberculosis. Angew Chem Int
Ed.
https://doi.org/10.1002/anie.
202000523
44. Daffe ´ M, Lane ´elle MA (1988) Distribution of
phthiocerol diester, phenolic mycosides and
Lipid and Lipoarabinomannan
149
lipids. J Lipid Res 48:1976–1984
22. Hsu FF, Soehl K, Turk J et al (2011) Characterization of mycolic acids from the pathogen
Rhodococcus equi by tandem mass spectrometry
with electrospray ionization. Anal Biochem
409:112–122
23. Daffe ´ M, Lane ´elle MA, Puzo G (1983) Structural elucidation by field desorption and
electron-impact mass spectrometry of the
C-mycosides isolated from Mycobacterium
smegmatis.
Biochim
Biophys
Acta
751:439–443
24. Lopez-Marin LM, Prome ´ D, Lane ´elle MA et al
(1992) Fast-atom bombardment mass spectrometry of mycobacterial glycopeptidolipid
antigens: structural characterization by charge
remote fragmentation. J Am Soc Mass Spectrom 3:656–661
25. Lopez-Marin LM, Lane ´elle MA, Prome ´ D et al
(1992) Structure of a novel sulfate-containing
mycobacterial
glycolipid.
Biochemistry
31:11106–11111
26. Hsu FF, Pacheco S, Turk J et al (2012) Structural determination of glycopeptidolipids of
Mycobacterium smegmatis by high resolution
multiple-stage linear ion-trap mass spectrometry with electrospray ionization. J Mass Spectrom 47:1269–1281
27. Gilleron M, Quesniaux VFJ, Puzo G (2003)
Acylation state of the phosphatidylinositol hexamannosides from Mycobacterium bovis BCG
and Mycobacterium tuberculosis H37Rv and its
implication in toll-like receptor response. J Biol
Chem 278:29880–29889
28. Gilleron M, Lindner B, Puzo G (2006)
MS/MS approach for characterization of the
fatty acid distribution on mycobacterial phosphatidyl-myo-inositol mannosides. Anal Chem
78:8543–8548
29. Layre E, Gala-De Paepe D, Larrouy-Maumus
G et al (2011) Deciphering sulfoglycolipids of
Mycobacterium tuberculosis. J Lipid Res
52:1098–1110
30. Hsu FF, Turk J (2004) Studies on sulfatides by
quadrupole ion-trap mass spectrometry with
electrospray ionization: structural characterization and the fragment processes that include an
unusual internal galactose residue loss and the
classical charge remote fragmentation. J Am
Soc Mass Spectrom 15:536–546
31. Rhoades RR, Streeter C, Turk J et al (2011)
Characterization of sulfolipids of Mycobacterium tuberculosis H37Rv by multiple-stage linear ion trap high resolution mass spectrometry
with electrospray ionization reveals that family
of sulfolipid II predominates. Biochemistry
50:9135–9147
32. Camacho LR, Constant P, Raynaud C et al
(2001) Analysis of the phthiocerol dimycocerosate locus of Mycobacterium tuberculosis: evidence that this lipid is involved in the cell wall
permeability
barrier.
J
Biol
Chem
276:19845–19854
33. Constant P, Perez E, Malaga W et al (2002)
Role of the pks15/1 gene in the biosynthesis of
phenolglycolipids in the Mycobacterium tuberculosis
complex.
J
Biol
Chem
277:38148–38158
34. Fujita Y, Naka T, Doi T et al (2005a) Direct
molecular mass determination of trehalose
monomycolates from 11 species of mycobacteria by MALDI-TOF mass spectrometry.
Microbiology 151:1443–1425
35. Fujita Y, Naka T, McNeil MR et al (2005b)
Intact molecular characterization of cord factor
(trehalose 6,6
0 -dimycolatee) from nine species
of mycobacteria by MALDI-TOF mass spectrometry. Microbiology 151:3403–3416
36. Hsu FF, Wohlmann J, Turk J et al (2012)
Structural
definition
of
trehalose
6-monomycolates
and
trehalose
6,60 -dimycolates from the pathogen Rhodococcus
equi by multiple-stage linear ion-trap mass
spectrometry with electrospray ionization. J
Am Soc Mass Spectrom 22:2160–2170
37. Asselineau C, Tocanne G, Tocanne JF (1970)
Ste ´re ´ochimie des acides mycoliques. Bull Soc
Chim Fr 4:1455–1459
38. Rafidinarivo E, Prome ´ JC, Le ´vy-Fre ´bault V
(1985) New kinds of unsaturated mycolic
acids from Mycobacterium fallax sp. nov.
Chem Phys Lipids 36:215–228
39. Lacave C, Lane ´elle MA, Daffe ´ et al (1987)
Structure and metabolic study of the mycolic
acids of Mycobacterium fortuitum. Eur J Biochem 163:369–378
40. Lane ´elle MA, Lacave C, Daffe ´ M et al (1988)
Mycolic acids of Mycobacterium aurum. Structure and biogenetic implications. Eur J Biochem 177:631–635
41. Lane ´elle MA, Lacave C, Daffe ´ M et al (1989)
Mycolic acid metabolic filiation and location in
Mycobacterium aurum and Mycobacterium
phlei. Eur J Biochem 181:459–466
42. Daffe ´ M, Lane ´elle MA, Lacave C (1991) Structure and stereochemistry of mycolic acids of
Mycobacterium marinum and Mycobacterium
ulcerans. Res Microbiol 142:397–403
43. Tahiri N, Fodran P, Jayaraman D, Buter J et al
(2020) Total synthesis of a mycolic acid from
Mycobacterium tuberculosis. Angew Chem Int
Ed.
https://doi.org/10.1002/anie.
202000523
44. Daffe ´ M, Lane ´elle MA (1988) Distribution of
phthiocerol diester, phenolic mycosides and
Lipid and Lipoarabinomannan
149