KEGG   ORTHOLOGY: K22114
Entry
K22114                      KO                                     
Symbol
ddaF
Name
dapdiamide synthase [EC:6.3.2.47]
Pathway
map00998  Biosynthesis of various antibiotics
map01100  Metabolic pathways
map01110  Biosynthesis of secondary metabolites
Module
M00904  Dapdiamides biosynthesis, L-2,3-diaminopropanoate => dapdiamide A/B/C
Brite
KEGG Orthology (KO) [BR:ko00001]
 09100 Metabolism
  09110 Biosynthesis of other secondary metabolites
   00998 Biosynthesis of various antibiotics
    K22114  ddaF; dapdiamide synthase
Enzymes [BR:ko01000]
 6. Ligases
  6.3  Forming carbon-nitrogen bonds
   6.3.2  Acid-D-amino-acid ligases (peptide synthases)
    6.3.2.47  dapdiamide synthase
     K22114  ddaF; dapdiamide synthase
Other DBs
RN: R10942 R10943 R10944
Genes
SPE: Spro_0344
SPLY: Q5A_016905(purD_2)
PVA: Pvag_pPag20162 Pvag_pPag20163
PAGC: BEE12_22710
PPEE: I6G31_07780
PAEW: KIH87_15140 KIH87_15180
KIA: G8A07_15070
AG: ADN39488(ddaF)
Reference
  Authors
Hollenhorst MA, Clardy J, Walsh CT
  Title
The ATP-dependent amide ligases DdaG and DdaF assemble the fumaramoyl-dipeptide scaffold of the dapdiamide antibiotics.
  Journal
Biochemistry 48:10467-72 (2009)
DOI:10.1021/bi9013165
  Sequence
LinkDB

KEGG   ENZYME: 6.3.2.47
Entry
EC 6.3.2.47                 Enzyme                                 
Name
dapdiamide synthase;
DdaF;
dapdiamide A synthase
Class
Ligases;
Forming carbon-nitrogen bonds;
Acid-D-amino-acid ligases (peptide synthases)
Sysname
3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanine:L-valine ligase (ADP-forming)
Reaction(IUBMB)
(1) ATP + 3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanine + L-valine = ADP + phosphate + 3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanyl-L-valine [RN:R10942];
(2) ATP + 3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanine + L-isoleucine = ADP + phosphate + 3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanyl-L-isoleucine [RN:R10943];
(3) ATP + 3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanine + L-leucine = ADP + phosphate + 3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanyl-L-leucine [RN:R10944];
(4) ATP + 3-({[(2R,3R)-3-carbamoyloxiran-2-yl]carbonyl}amino)-L-alanine + L-valine = ADP + phosphate + 3-({[(2R,3R)-3-carbamoyloxiran-2-yl]carbonyl}amino)-L-alanyl-L-valine [RN:R10941]
Reaction(KEGG)
Substrate
ATP [CPD:C00002];
3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanine [CPD:C20966];
L-valine [CPD:C00183];
L-isoleucine [CPD:C00407];
L-leucine [CPD:C00123];
3-({[(2R,3R)-3-carbamoyloxiran-2-yl]carbonyl}amino)-L-alanine [CPD:C20967]
Product
ADP [CPD:C00008];
phosphate [CPD:C00009];
3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanyl-L-valine [CPD:C20962];
3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanyl-L-isoleucine [CPD:C20963];
3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanyl-L-leucine [CPD:C20964];
3-({[(2R,3R)-3-carbamoyloxiran-2-yl]carbonyl}amino)-L-alanyl-L-valine [CPD:C20965]
Comment
The enzyme, characterized from the bacterium Pantoea agglomerans, is involved in biosynthesis of dapdiamide tripeptide antibiotics, a family of fumaramoyl- and epoxysuccinamoyl-peptides named for the presence of an (S)-2,3-diaminopropanoate (DAP) moiety and two amide linkages in their scaffold.
History
EC 6.3.2.47 created 2015, modified 2016
Pathway
ec00998  Biosynthesis of various antibiotics
ec01100  Metabolic pathways
ec01110  Biosynthesis of secondary metabolites
Orthology
K22114  dapdiamide synthase
Genes
SPESpro_0344
SPLYQ5A_016905(purD_2)
PVAPvag_pPag20162 Pvag_pPag20163
PAGCBEE12_22710
PPEEI6G31_07780
PAEWKIH87_15140 KIH87_15180
KIAG8A07_15070
Reference
1  [PMID:19807062]
  Authors
Hollenhorst MA, Clardy J, Walsh CT
  Title
The ATP-dependent amide ligases DdaG and DdaF assemble the fumaramoyl-dipeptide scaffold of the dapdiamide antibiotics.
  Journal
Biochemistry 48:10467-72 (2009)
DOI:10.1021/bi9013165
  Sequence
Reference
2  [PMID:20945916]
  Authors
Hollenhorst MA, Bumpus SB, Matthews ML, Bollinger JM Jr, Kelleher NL, Walsh CT
  Title
The nonribosomal peptide synthetase enzyme DdaD tethers N(beta)-fumaramoyl-l-2,3-diaminopropionate for Fe(II)/alpha-ketoglutarate-dependent epoxidation by DdaC during dapdiamide antibiotic biosynthesis.
  Journal
J Am Chem Soc 132:15773-81 (2010)
DOI:10.1021/ja1072367
  Sequence
Other DBs
ExplorEnz - The Enzyme Database: 6.3.2.47
IUBMB Enzyme Nomenclature: 6.3.2.47
ExPASy - ENZYME nomenclature database: 6.3.2.47
BRENDA, the Enzyme Database: 6.3.2.47
LinkDB

KEGG   REACTION: R10943
Entry
R10943                      Reaction                               
Name
3-{[(2E)-4-amino-4-oxobut-2-enoyl]amino}-L-alanine:L-isoleucine ligase (ADP-forming)
Definition
ATP + 3-{[(2E)-4-Amino-4-oxobut-2-enoyl]amino}-L-alanine + L-Isoleucine <=> ADP + Orthophosphate + Dapdiamide B
Equation
Enzyme
Pathway
rn00998  Biosynthesis of various antibiotics
rn01100  Metabolic pathways
rn01110  Biosynthesis of secondary metabolites
Module
M00904  Dapdiamides biosynthesis, L-2,3-diaminopropanoate => dapdiamide A/B/C
Orthology
K22114  dapdiamide synthase [EC:6.3.2.47]
Other DBs
RHEA: 44351
LinkDB

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