129
was no significant change observed in the rate of uptake of this molecule into the
fungal cell. Furthermore, the authors suggested that the iron coordination centre and
its residues might play a significant role in siderophore transport in fungal cells. The
structure of the compound was confirmed on the basis of spectral analysis but the
complete structure of the compound has not been given (Deml et al. 1984).
All fungal hydroxamate ferrichrome siderophores contains cyclic hexapeptide
moieties with six L-amino acids, among three of peptides having attachment of
trishydroxamate residues. The attachment of hydroxamate with three peptides are
Table 8.2 Fungal hydroxamate ferrichrome siderophores
Ferrichromes
The amino acid
substitutions
Acylating acid in ornithyl δ-N-acyl groups
Asperchrome A (18)
Ser-ala-Gly
Trans-β-methylglutaconlylic acid
Asperchrome B1 (19) Ser 1 -Ser 2 -Gly
Two groups derived from trans-5-hydroxy-3methyl- Z-pentenoic acid and one group from
acetic acid
Asperchrome B2 (20) Ser 1 -Ser 2 -Gly
Two groups derived from trans-5-hydroxy-3methyl- Z-pentenoic acid and one group from
acetic acid
Asperchrome B3 (21) Ser 1 -Ser 2 -Gly
a
Asperchrome C (22)
Ser 1 -Ser 2 -Gly
a
Asperchrome D1 (23) Ser 1 -Ser 2 -Gly
Two groups derived from acetic acid and one
group from trans-5-hydroxy-3-methyl-Zpentenoic acid
Asperchrome D2 (24) Ser 1 -Ser 2 -Gly
a
Asperchrome D3 (25) Ser 1 -Ser 2 -Gly
a
Asperchrome E (26)
Ser 1 -Ser 2 -Gly
a
Asperchrome F1 (27) Ser 1 -Ser 2 -Gly
a
Asperchrome F2 (28) Ser 1 -Ser 2 -Gly
a
Asperchrome F3 (29) Ser 1 -Ser 2 -Gly
a
Ferrichrome (30)
Gly 1 -Gly 2 -Gly 3
Acetic acid
Ferrichrome A (31)
Ser 1 -Ser 2 -Gly
trans-β-methylglutaconic acid
Ferrichrome C (32)
Gly-ala-Gly
Acetic acid
Ferrichrysin (17)
Ser 1 -Ser 2 -Gly
Acetic acid
Ferricrocin (33)
Gly 1 -Ser-Gly 2
Acetic acid
Ferrirhodin (34)
Ser 1 -Ser 2 -Gly
cis-5-hydroxy-3-methyl-Z-pentenoic acid
Or cis-anhydromevalonoylic acid
Ferrirubin (35)
Ser 1 -Ser 2 -Gly
trans-5-hydroxy-3-methyl-Z-pentenoic acid
Or trans-anhydromevalonoylic acid
Malonichrome (36)
Ala-Gly 1 -Gly 2
Malonic acid
Sake colorant A (37)
Ser-ala-Gly
a
Tetraglycyl
ferrichrome (38)
Gly-Gly-Gly-Gly cis-anhydromevalonic acid
Des(diserylglycyl)
ferrirhodin (39)
Acetic acid
a Not confirmed
8 Chemistry and Biomedical Applications of Fungal Siderophores
was no significant change observed in the rate of uptake of this molecule into the
fungal cell. Furthermore, the authors suggested that the iron coordination centre and
its residues might play a significant role in siderophore transport in fungal cells. The
structure of the compound was confirmed on the basis of spectral analysis but the
complete structure of the compound has not been given (Deml et al. 1984).
All fungal hydroxamate ferrichrome siderophores contains cyclic hexapeptide
moieties with six L-amino acids, among three of peptides having attachment of
trishydroxamate residues. The attachment of hydroxamate with three peptides are
Table 8.2 Fungal hydroxamate ferrichrome siderophores
Ferrichromes
The amino acid
substitutions
Acylating acid in ornithyl δ-N-acyl groups
Asperchrome A (18)
Ser-ala-Gly
Trans-β-methylglutaconlylic acid
Asperchrome B1 (19) Ser 1 -Ser 2 -Gly
Two groups derived from trans-5-hydroxy-3methyl- Z-pentenoic acid and one group from
acetic acid
Asperchrome B2 (20) Ser 1 -Ser 2 -Gly
Two groups derived from trans-5-hydroxy-3methyl- Z-pentenoic acid and one group from
acetic acid
Asperchrome B3 (21) Ser 1 -Ser 2 -Gly
a
Asperchrome C (22)
Ser 1 -Ser 2 -Gly
a
Asperchrome D1 (23) Ser 1 -Ser 2 -Gly
Two groups derived from acetic acid and one
group from trans-5-hydroxy-3-methyl-Zpentenoic acid
Asperchrome D2 (24) Ser 1 -Ser 2 -Gly
a
Asperchrome D3 (25) Ser 1 -Ser 2 -Gly
a
Asperchrome E (26)
Ser 1 -Ser 2 -Gly
a
Asperchrome F1 (27) Ser 1 -Ser 2 -Gly
a
Asperchrome F2 (28) Ser 1 -Ser 2 -Gly
a
Asperchrome F3 (29) Ser 1 -Ser 2 -Gly
a
Ferrichrome (30)
Gly 1 -Gly 2 -Gly 3
Acetic acid
Ferrichrome A (31)
Ser 1 -Ser 2 -Gly
trans-β-methylglutaconic acid
Ferrichrome C (32)
Gly-ala-Gly
Acetic acid
Ferrichrysin (17)
Ser 1 -Ser 2 -Gly
Acetic acid
Ferricrocin (33)
Gly 1 -Ser-Gly 2
Acetic acid
Ferrirhodin (34)
Ser 1 -Ser 2 -Gly
cis-5-hydroxy-3-methyl-Z-pentenoic acid
Or cis-anhydromevalonoylic acid
Ferrirubin (35)
Ser 1 -Ser 2 -Gly
trans-5-hydroxy-3-methyl-Z-pentenoic acid
Or trans-anhydromevalonoylic acid
Malonichrome (36)
Ala-Gly 1 -Gly 2
Malonic acid
Sake colorant A (37)
Ser-ala-Gly
a
Tetraglycyl
ferrichrome (38)
Gly-Gly-Gly-Gly cis-anhydromevalonic acid
Des(diserylglycyl)
ferrirhodin (39)
Acetic acid
a Not confirmed
8 Chemistry and Biomedical Applications of Fungal Siderophores