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EC Tree
IUBMB Comments A flavoprotein from the bacterium Streptomyces noursei. The enzyme can also oxidize several other cyclo dipeptides, the best being cyclo(L-tryptophyl-L-tryptophyl) and cyclo(L-phenylalanyl-L-phenylalanyl) [1,2].
The enzyme appears in viruses and cellular organisms
Synonyms
AlbA, cyclic dipeptide oxidase, cyclo(dipeptide):oxygen oxidoreductase,
more
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cyclo(dipeptide):oxygen oxidoreductase
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AlbA
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cyclic dipeptide oxidase
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cyclic dipeptide oxidase
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cyclic dipeptide oxidase
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cyclo(L-leucyl-L-phenylalanyl) + 2 O2 = albonoursin + 2 H2O2
overall reaction
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cyclo(L-leucyl-L-phenylalanyl) + O2 = cyclo[(Z)-alpha,beta-didehydrophenylalanyl-L-leucyl] + H2O2
(1a)
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cyclo[(Z)-alpha,beta-didehydrophenylalanyl-L-leucyl] + O2 = albonoursin + H2O2
(1b)
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cyclo(L-leucyl-L-phenylalanyl):oxygen oxidoreductase
A flavoprotein from the bacterium Streptomyces noursei. The enzyme can also oxidize several other cyclo dipeptides, the best being cyclo(L-tryptophyl-L-tryptophyl) and cyclo(L-phenylalanyl-L-phenylalanyl) [1,2].
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cyclo(L-4-O-methyltyrosine-L-leucine) + 2 O2
? + 2 H2O2
cyclo(L-Glu-Gly) + O2
(4Z)-4-(3,6-dioxopiperazin-2-yl)butanoate + H2O2
cyclo(L-Leu-Gly) + O2
(3Z)-3-(2-methylpropylidene)piperazine-2,5-dione + H2O2
cyclo(L-Leu-L-Ala) + O2
?
13% mono-dehydro-products and 4% bis-dehydro products
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?
cyclo(L-Leu-L-Phe) + O2
albonoursin + H2O2
cyclo(L-Leu-L-Phe) + O2
cyclo[(Z)-alpha,beta-didehydrophenylalanyl-L-leucyl] + H2O2
cyclo(L-leucyl-L-phenylalanyl) + 2 O2
albonoursin + 2 H2O2
cyclo(L-leucyl-L-phenylalanyl) + O2
albonoursin + H2O2
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ir
cyclo(L-Phe-Gly) + O2
(3Z)-3-benzylidenepiperazine-2,5-dione + H2O2
36% mono-dehydro-products and no bis-dehydro products
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?
cyclo(L-Phe-L-His) + O2
?
21% mono-dehydro-products and less than 1% bis-dehydro products
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?
cyclo(L-Ser-Gly) + O2
(3Z)-3-(2-hydroxyethylidene)piperazine-2,5-dione + H2O2
11% mono-dehydro-products and no bis-dehydro products
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?
cyclo(L-Trp-L-Trp) + O2
?
74% mono-dehydro-products and 14% bis-dehydro products
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?
cyclo[(Z)-alpha,beta-didehydrophenylalanyl-L-leucyl] + O2
albonoursin + H2O2
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?
additional information
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cyclo(L-4-O-methyltyrosine-L-leucine) + 2 O2
? + 2 H2O2
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?
cyclo(L-4-O-methyltyrosine-L-leucine) + 2 O2
? + 2 H2O2
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?
cyclo(L-Glu-Gly) + O2
(4Z)-4-(3,6-dioxopiperazin-2-yl)butanoate + H2O2
3% mono-dehydro-products and no bis-dehydro products
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?
cyclo(L-Glu-Gly) + O2
(4Z)-4-(3,6-dioxopiperazin-2-yl)butanoate + H2O2
3% mono-dehydro-products and no bis-dehydro products
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?
cyclo(L-Leu-Gly) + O2
(3Z)-3-(2-methylpropylidene)piperazine-2,5-dione + H2O2
9% mono-dehydro-products and no bis-dehydro products
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?
cyclo(L-Leu-Gly) + O2
(3Z)-3-(2-methylpropylidene)piperazine-2,5-dione + H2O2
9% mono-dehydro-products and no bis-dehydro products
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?
cyclo(L-Leu-L-Phe) + O2
albonoursin + H2O2
the catalytic reaction of the natural substrate cyclo(L-leucyl-L-phenylalanyl) occurs in a two-step sequential reaction leading first to cyclo(alpha,beta-dehydro-Phe-L-Leu) and finally to albonoursin
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cyclo(L-Leu-L-Phe) + O2
albonoursin + H2O2
the catalytic reaction of the natural substrate cyclo(L-leucyl-L-phenylalanyl) occurs in a two-step sequential reaction leading first to cyclo(alpha,beta-dehydro-Phe-L-Leu) and finally to albonoursin
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?
cyclo(L-Leu-L-Phe) + O2
cyclo[(Z)-alpha,beta-didehydrophenylalanyl-L-leucyl] + H2O2
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?
cyclo(L-Leu-L-Phe) + O2
cyclo[(Z)-alpha,beta-didehydrophenylalanyl-L-leucyl] + H2O2
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?
cyclo(L-leucyl-L-phenylalanyl) + 2 O2
albonoursin + 2 H2O2
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?
cyclo(L-leucyl-L-phenylalanyl) + 2 O2
albonoursin + 2 H2O2
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?
additional information
?
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albonoursin is then methoxylated to cyclo(L-methoxytyrosine-L-leucine) by O-methyltranferases, encoded by genes B005_4460 and B005_4464, termed albM1 and albM2
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?
additional information
?
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albonoursin is then methoxylated to cyclo(L-methoxytyrosine-L-leucine) by O-methyltranferases, encoded by genes B005_4460 and B005_4464, termed albM1 and albM2
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?
additional information
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no activity towards N-acetyl-L-Phe-L-Leu and N-actely-L-Leu-L-Phe
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?
additional information
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no activity towards N-acetyl-L-Phe-L-Leu and N-actely-L-Leu-L-Phe
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?
additional information
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no activity towards N-acetyl-L-Phe-L-Leu and N-actely-L-Leu-L-Phe
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?
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cyclo(L-4-O-methyltyrosine-L-leucine) + 2 O2
? + 2 H2O2
cyclo(L-Leu-L-Phe) + O2
albonoursin + H2O2
cyclo(L-Leu-L-Phe) + O2
cyclo[(Z)-alpha,beta-didehydrophenylalanyl-L-leucyl] + H2O2
cyclo(L-leucyl-L-phenylalanyl) + 2 O2
albonoursin + 2 H2O2
cyclo(L-leucyl-L-phenylalanyl) + O2
albonoursin + H2O2
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ir
cyclo(L-4-O-methyltyrosine-L-leucine) + 2 O2
? + 2 H2O2
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?
cyclo(L-4-O-methyltyrosine-L-leucine) + 2 O2
? + 2 H2O2
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?
cyclo(L-Leu-L-Phe) + O2
albonoursin + H2O2
the catalytic reaction of the natural substrate cyclo(L-leucyl-L-phenylalanyl) occurs in a two-step sequential reaction leading first to cyclo(alpha,beta-dehydro-Phe-L-Leu) and finally to albonoursin
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cyclo(L-Leu-L-Phe) + O2
albonoursin + H2O2
the catalytic reaction of the natural substrate cyclo(L-leucyl-L-phenylalanyl) occurs in a two-step sequential reaction leading first to cyclo(alpha,beta-dehydro-Phe-L-Leu) and finally to albonoursin
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cyclo(L-Leu-L-Phe) + O2
cyclo[(Z)-alpha,beta-didehydrophenylalanyl-L-leucyl] + H2O2
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cyclo(L-Leu-L-Phe) + O2
cyclo[(Z)-alpha,beta-didehydrophenylalanyl-L-leucyl] + H2O2
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?
cyclo(L-leucyl-L-phenylalanyl) + 2 O2
albonoursin + 2 H2O2
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cyclo(L-leucyl-L-phenylalanyl) + 2 O2
albonoursin + 2 H2O2
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?
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NaCl
about 50% residual activity in the presence of 1 M NaCl, about 30% residual activity in the presence of 2 M NaCl, about 10% residual activity in the presence of 4 M NaCl, about 3.5% residual activity in the presence of 6 M NaCl
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0.053
cyclo(L-Leu-L-Phe)
in 100 mM Tris/HCl buffer, pH 8.0, at 30°C
0.067
cyclo(L-Phe-L-His)
in 100 mM Tris/HCl buffer, pH 8.0, at 30°C
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0.69
cyclo(L-Leu-L-Phe)
in 100 mM Tris/HCl buffer, pH 8.0, at 30°C
0.453
cyclo(L-Phe-L-His)
in 100 mM Tris/HCl buffer, pH 8.0, at 30°C
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60
activity increases up to the maximum at 60°C followed by a substantial drop above this temperature
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isolated from the guts of healthy honeybees in a year-round survey
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brenda
isolated from the guts of healthy honeybees in a year-round survey
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brenda
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UniProt
brenda
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UniProt
brenda
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malfunction
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the albABC gene operon deletion mutant of Nocariopsis alba cannot produce cyclic dipeptides, cyclo(DELTAPhe-DELTALeu) i.e. albonoursin, and cyclo(DELTAmTyr-DELTALeu)
malfunction
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the albABC gene operon deletion mutant of Nocariopsis alba cannot produce cyclic dipeptides, cyclo(DELTAPhe-DELTALeu) i.e. albonoursin, and cyclo(DELTAmTyr-DELTALeu)
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metabolism
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the albonoursin biosynthetic gene cluster is involved in the regulated biosynthesis of antibacterial cyclic dipeptides in Nocardiopsis alba
metabolism
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the albonoursin biosynthetic gene cluster is involved in the regulated biosynthesis of antibacterial cyclic dipeptides in Nocardiopsis alba
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physiological function
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the enzyme is required for biosynthesis of antibacterial cyclic dipeptides, cyclo(DELTAPhe-DELTALeu) i.e. albonoursin, and cyclo(DELTAmTyr-DELTALeu)
physiological function
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the enzyme is required for biosynthesis of antibacterial cyclic dipeptides, cyclo(DELTAPhe-DELTALeu) i.e. albonoursin, and cyclo(DELTAmTyr-DELTALeu)
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ALBA_STRNR
219
0
23763
Swiss-Prot
-
A0A1V6K7J3_9BACT
175
0
19910
TrEMBL
-
A0A1V5SXN5_9BACT
173
0
19087
TrEMBL
-
A0A1V5D706_9DELT
185
0
20589
TrEMBL
-
A0A7J0AVY3_9BACT
204
0
22062
TrEMBL
-
A0A1V4IJ28_9CLOT
174
0
19723
TrEMBL
-
A0A1V5U7W3_9BACT
203
0
21824
TrEMBL
-
A0A6N3I0Q7_9CLOT
174
0
19992
TrEMBL
-
A0A0P8W1M1_9CLOT
187
0
21218
TrEMBL
-
A0A0M2H6R5_9MICO
193
0
20539
TrEMBL
-
A0A1V5YKY6_9CHLR
172
0
18375
TrEMBL
-
A0A517DPU8_9FIRM
172
0
19175
TrEMBL
-
A0A0J6YMW2_9MYCO
236
0
26586
TrEMBL
-
A0A7J0AA44_9BACT
180
0
19990
TrEMBL
-
A0A1V6GE41_9BACT
176
0
19061
TrEMBL
-
A0A174UI46_PHOVU
166
0
18878
TrEMBL
-
A0A1V5IQ28_9BACT
174
0
19544
TrEMBL
-
A0A645A1U1_9ZZZZ
179
0
19428
TrEMBL
other Location (Reliability: 2 )
A0A1V5G3Q8_9BACT
172
0
19917
TrEMBL
-
A0A1V6F027_9BACT
182
0
20904
TrEMBL
-
A0A644UBY3_9ZZZZ
168
0
19134
TrEMBL
other Location (Reliability: 3 )
A0A2T0BEC8_9CLOT
181
0
20394
TrEMBL
-
A0A6N2U2R8_9FIRM
uncultured Anaerotruncus sp
172
0
19169
TrEMBL
-
A0A1V4IBE8_9FIRM
170
0
19251
TrEMBL
-
A0A6N8I1T6_9FIRM
174
0
19723
TrEMBL
-
A0A1V6JIC6_9BACT
175
0
19302
TrEMBL
-
A0A136WGY7_9FIRM
168
0
19077
TrEMBL
-
A0A485LZ09_9ZZZZ
184
0
19968
TrEMBL
other Location (Reliability: 1 )
A0A1V5H6A5_9DELT
184
0
19976
TrEMBL
-
A0A5S9R9P8_MYCVN
202
0
22221
TrEMBL
-
A0A1V6JQC4_9BACT
193
0
21621
TrEMBL
-
A0A1V5QXT0_9PROT
170
0
18346
TrEMBL
-
A0A1D3UGI7_TANFO
168
0
19682
TrEMBL
-
A0A1V5V038_9BACT
186
2
21026
TrEMBL
-
A0A4Z0Y1H8_9FIRM
166
0
18586
TrEMBL
-
A0A1V5ZXB6_9BACT
178
0
19792
TrEMBL
-
A0A1V4WTI5_9DELT
202
0
21885
TrEMBL
-
A0A6N3FP49_FLAPL
174
0
19203
TrEMBL
-
A0A7J0A918_9BACT
224
0
23991
TrEMBL
-
A0A1E7RTL9_BUTME
169
0
19340
TrEMBL
-
A0A645DG05_9ZZZZ
169
0
18154
TrEMBL
Mitochondrion (Reliability: 4 )
A0A1V6GLI9_9BACT
169
0
18470
TrEMBL
-
A0A5C6EJY6_9BACT
168
0
18817
TrEMBL
-
A0A644TXJ3_9ZZZZ
175
0
19647
TrEMBL
other Location (Reliability: 2 )
A0A6N3GTI3_EUBLI
169
0
19354
TrEMBL
-
A0A1V5IL89_9ACTN
179
0
20134
TrEMBL
-
A0A0P0GAM0_9BACE
415
3
45914
TrEMBL
-
A0A1V4Y2J9_9DELT
185
0
20561
TrEMBL
-
A0A1V5HEJ8_9BACT
173
0
19966
TrEMBL
-
A0A0J6VP72_9MYCO
123
0
13464
TrEMBL
-
A0A1V5PUI9_9ACTN
167
0
19165
TrEMBL
-
A0A644ZJQ1_9ZZZZ
175
0
20002
TrEMBL
other Location (Reliability: 3 )
A0A1V5I3N9_9SPIR
186
0
20265
TrEMBL
-
A0A6V8LN23_9DELT
169
0
18602
TrEMBL
-
A0A1V6BFK6_9BACT
173
0
19521
TrEMBL
-
A0A1V5YEF6_9CHLR
168
0
18569
TrEMBL
-
A0A644YQP4_9ZZZZ
178
0
20468
TrEMBL
other Location (Reliability: 2 )
A0A6N2UY30_9FIRM
uncultured Anaerotruncus sp
190
0
20628
TrEMBL
-
A0A5S9PSF5_MYCVN
247
0
27552
TrEMBL
-
A0A168PNB3_9CLOT
180
0
20154
TrEMBL
-
A0A5C6D7B4_9BACT
168
0
18930
TrEMBL
-
A0A161XCD5_9CLOT
166
0
19108
TrEMBL
-
A0A6F9ZEG9_9BACT
167
0
19055
TrEMBL
-
A0A1F2PIL0_9FIRM
163
0
18170
TrEMBL
-
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21000
x * 21000, SDS-PAGE
21066
x * 21066, calculated from amino acid sequence
23000
x * 23000, SDS-PAGE
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?
x * 23000, SDS-PAGE
?
x * 21066, calculated from amino acid sequence
?
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x * 23000, SDS-PAGE
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?
-
x * 21066, calculated from amino acid sequence
-
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additional information
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generation of an albABC gene deletion mutant YL001 of Nocardiopsis alba, genetic organization, overview. Strain YL001 show no significant difference from the wild-type in colonial morphology, and it has a slightly vibrant growth on the MS agar, production of the cyclic dipeptides is abolished in the DELTAalbABC mutant
additional information
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generation of an albABC gene deletion mutant YL001 of Nocardiopsis alba, genetic organization, overview. Strain YL001 show no significant difference from the wild-type in colonial morphology, and it has a slightly vibrant growth on the MS agar, production of the cyclic dipeptides is abolished in the DELTAalbABC mutant
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6 - 8.7
the enzyme activity is quite stable at neutral and basic pH values, whereas it decreases at acidic pH values. Residual activity is 75% after 6.5 h at pH 6.0
722172
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-80°C, purified enzyme in the absence of any additive, several months, no loss of activity
22°C, purified enzyme in the absence of any additive, 24 h, no loss of activity
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ammonium sulfate precipitation, Q-Sepharose column chromatography, EMD propyl column chromatography, and Superose 6 gel filtration
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expressed in Escherichia coli BL21(DE3) cells
the enzyme is encoded in the albonoursin biosynthetic gene cluster, albABC, genes albAB encode units for a cyclic dipeptide oxidase complex, responsible for generating two dehydrogenated double bonds
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Lautru, S.; Gondry, M.; Genet, R.; Pernodet, J.L.
The albonoursin gene cluster of S. noursei biosynthesis of diketopiperazine metabolites independent of nonribosomal peptide synthetases
Chem. Biol.
9
1355-1364
2002
Streptomyces noursei (Q8GED9), Streptomyces noursei
brenda
Gondry, M.; Lautru, S.; Fusai, G.; Meunier, G.; Menez, A.; Genet, R.
Cyclic dipeptide oxidase from Streptomyces noursei. Isolation, purification and partial characterization of a novel, amino acyl alpha,beta-dehydrogenase
Eur. J. Biochem.
268
1712-1721
2001
Streptomyces noursei (Q8GED9), Streptomyces noursei, Streptomyces noursei ATCC 11455 (Q8GED9)
brenda
Li, Y.; Lai, Y.M.; Lu, Y.; Yang, Y.L.; Chen, S.
Analysis of the biosynthesis of antibacterial cyclic dipeptides in Nocardiopsis alba
Arch. Microbiol.
196
765-774
2014
Nocardiopsis alba, Nocardiopsis alba ATCC BAA-2165
brenda
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