0.4 μL of a 1 M sodium cyanoborohydride solution dissolved
in tetrahydrofuran for 90 min at 55
C. Stop the reaction by
adding 20 μL of water. Dissolve 1–5 μL of the APTS derivatives
solution in 20 μL water and inject the solution in capillary
electrophoresis in the reverse mode using acetic acid 1%
(w/v), triethylamine 30 mM in water, pH 3.5 as running
electrolyte.
References
1. Goren M, Brennan PJ (1979) Mycobacterial
lipids: chemistry and biological activities. In:
Youmans
GP
(ed)
Tuberculosis.
W.B. Saunders Company, Philadelphia, pp
63–193
2. Jarlier V, Nikaido H (1990) Permeability barrier to hydrophilic solutes in Mycobacterium
chelonei. J Bacteriol 172:1418–1423
3. Daffe ´ M, Zuber B (2014) The fascinating coat
surrounding mycobacteria. In: Remaut H,
Fronzes R (eds) Bacterial membranes: structural and molecular biology. Horizon Scientific
Press, Norfolk, pp 179–192
4. Marrakchi H, Lane ´elle MA, Daffe ´ M (2014)
Mycolic acids: structures, biosynthesis and
beyond. Chem Biol 21:67–45
5. Brennan PJ (1988) Mycobacterium and other
actinomycetes. In: Ratledge C, Wilkinson SG
(eds) Microbial lipids, vol 1. Academic Press,
London, pp 203–298
6. Daffe ´ M, Lemassu A (2000) Glycomicrobiology of the mycobacterial cell surface: structure
and biological activities of the cell envelope
glycoconjugates.
In:
Doyle
RJ
(ed) Glycomicrobiology. Plenum Press,
New York, pp 225–273
7. Minnikin DE, Kremer L, Dover LG et al
(2002) The methyl-branched fortifications of
Mycobacterium tuberculosis. Chem Biol
9:545–553
8. Asselineau J (1991) Bacterial lipids containing
amino acids of peptides linked by amide bonds.
In: Hertz W, Grisebach H, Kirby GW, Tamm C
(eds) Progress in the chemistry of organic natural products, vol 56. Sringer-Verlag, Vienna,
pp 1–85
9. Ete ´madi AH (1967) Isome ´risation de mycolates de me ´thyle en milieu alcalin. Chem Phys
Lipids 1:165–175
10. Toubiana R, Berlan J, Sato H et al (1979)
Three types of mycolic acid from Mycobacterium tuberculosis Bre ´vanne: implications for
structure-function relationships in pathogenesis. J Bacteriol 139:205–211
11. Daffe ´ M, Lane ´elle MA, Puzo G et al (1981)
Acide mycolique e ´poxydique: un nouveau type
d’acide
mycolique.
Tetrahedron
Lett
22:4515–4516
12. Minnikin DE, Minnikin SM, Goodfellow M
(1982) The oxygenated mycolic acids of Mycobacterium fortuitum, M. farcinogenes and
M. senegalense. Biochim Biophys Acta
712:616–620
13. Odham G, Stenhagen E (1972) Fatty acids. In:
Waller GR (ed) Biochemical applications of
mass spectrometry. Wiley Interscience,
New York, pp 211–228
14. Asselineau J, Ryhage R, Stenhagen E (1957)
Mass spectrometry studies of long chain methyl
esters. A determination of the molecular
weight and structure of mycocerosic acid.
Acta Chem Scand 11:196–198
15. Ryhage R, St€ allerg-Stenhagen S, Stenhagen E
(1961) Esters of phthienoic acids. Ark Kemi
18:179–188
16. Puzo G, Prome ´ JC (1973) Fragmentation des
alde ´hydes cyclopropaniques en spectrome ´trie
de masse. Intervention d’interactions bifonctionnelles. Tetrahedron 29:3619–3629
17. Asselineau C, Clavel S, Cle ´ment F et al (1981)
Constituants lipidiques de Mycobacterium
leprae isole ´ de tatou infecte ´ expe ´rimentalement. Ann Microbiol (Paris) 132A:19–30
18. Que ´mard A, Lane ´elle MA, Marrakchi H et al
(1997) Structure of a hydroxymycolic acid
potentially involved in the synthesis of oxygenated mycolic acids of the Mycobacterium
tuberculosis complex. Eur J Biochem
250:758–763
19. Watanabe M, Aoyagi Y, Mitome H et al (2002)
Location of functional groups in mycobacterial
meromycolate chains; the recognition of new
structural principles in mycolic acids. Microbiology 148:1881–1902
20. Laval F, Lane ´elle MA, De ´on C et al (2001)
Accurate molecular mass determination of
mycolic acids by MALDI-TOF mass spectrometry. Anal Chem 73:4537–4544
148
Marie-Antoinette Lane ´ elle et al.
in tetrahydrofuran for 90 min at 55
C. Stop the reaction by
adding 20 μL of water. Dissolve 1–5 μL of the APTS derivatives
solution in 20 μL water and inject the solution in capillary
electrophoresis in the reverse mode using acetic acid 1%
(w/v), triethylamine 30 mM in water, pH 3.5 as running
electrolyte.
References
1. Goren M, Brennan PJ (1979) Mycobacterial
lipids: chemistry and biological activities. In:
Youmans
GP
(ed)
Tuberculosis.
W.B. Saunders Company, Philadelphia, pp
63–193
2. Jarlier V, Nikaido H (1990) Permeability barrier to hydrophilic solutes in Mycobacterium
chelonei. J Bacteriol 172:1418–1423
3. Daffe ´ M, Zuber B (2014) The fascinating coat
surrounding mycobacteria. In: Remaut H,
Fronzes R (eds) Bacterial membranes: structural and molecular biology. Horizon Scientific
Press, Norfolk, pp 179–192
4. Marrakchi H, Lane ´elle MA, Daffe ´ M (2014)
Mycolic acids: structures, biosynthesis and
beyond. Chem Biol 21:67–45
5. Brennan PJ (1988) Mycobacterium and other
actinomycetes. In: Ratledge C, Wilkinson SG
(eds) Microbial lipids, vol 1. Academic Press,
London, pp 203–298
6. Daffe ´ M, Lemassu A (2000) Glycomicrobiology of the mycobacterial cell surface: structure
and biological activities of the cell envelope
glycoconjugates.
In:
Doyle
RJ
(ed) Glycomicrobiology. Plenum Press,
New York, pp 225–273
7. Minnikin DE, Kremer L, Dover LG et al
(2002) The methyl-branched fortifications of
Mycobacterium tuberculosis. Chem Biol
9:545–553
8. Asselineau J (1991) Bacterial lipids containing
amino acids of peptides linked by amide bonds.
In: Hertz W, Grisebach H, Kirby GW, Tamm C
(eds) Progress in the chemistry of organic natural products, vol 56. Sringer-Verlag, Vienna,
pp 1–85
9. Ete ´madi AH (1967) Isome ´risation de mycolates de me ´thyle en milieu alcalin. Chem Phys
Lipids 1:165–175
10. Toubiana R, Berlan J, Sato H et al (1979)
Three types of mycolic acid from Mycobacterium tuberculosis Bre ´vanne: implications for
structure-function relationships in pathogenesis. J Bacteriol 139:205–211
11. Daffe ´ M, Lane ´elle MA, Puzo G et al (1981)
Acide mycolique e ´poxydique: un nouveau type
d’acide
mycolique.
Tetrahedron
Lett
22:4515–4516
12. Minnikin DE, Minnikin SM, Goodfellow M
(1982) The oxygenated mycolic acids of Mycobacterium fortuitum, M. farcinogenes and
M. senegalense. Biochim Biophys Acta
712:616–620
13. Odham G, Stenhagen E (1972) Fatty acids. In:
Waller GR (ed) Biochemical applications of
mass spectrometry. Wiley Interscience,
New York, pp 211–228
14. Asselineau J, Ryhage R, Stenhagen E (1957)
Mass spectrometry studies of long chain methyl
esters. A determination of the molecular
weight and structure of mycocerosic acid.
Acta Chem Scand 11:196–198
15. Ryhage R, St€ allerg-Stenhagen S, Stenhagen E
(1961) Esters of phthienoic acids. Ark Kemi
18:179–188
16. Puzo G, Prome ´ JC (1973) Fragmentation des
alde ´hydes cyclopropaniques en spectrome ´trie
de masse. Intervention d’interactions bifonctionnelles. Tetrahedron 29:3619–3629
17. Asselineau C, Clavel S, Cle ´ment F et al (1981)
Constituants lipidiques de Mycobacterium
leprae isole ´ de tatou infecte ´ expe ´rimentalement. Ann Microbiol (Paris) 132A:19–30
18. Que ´mard A, Lane ´elle MA, Marrakchi H et al
(1997) Structure of a hydroxymycolic acid
potentially involved in the synthesis of oxygenated mycolic acids of the Mycobacterium
tuberculosis complex. Eur J Biochem
250:758–763
19. Watanabe M, Aoyagi Y, Mitome H et al (2002)
Location of functional groups in mycobacterial
meromycolate chains; the recognition of new
structural principles in mycolic acids. Microbiology 148:1881–1902
20. Laval F, Lane ´elle MA, De ´on C et al (2001)
Accurate molecular mass determination of
mycolic acids by MALDI-TOF mass spectrometry. Anal Chem 73:4537–4544
148
Marie-Antoinette Lane ´ elle et al.