4-hydroxymandelate synthase

Details

Name
4-hydroxymandelate synthase
Kind
protein
Synonyms
  • 1.13.11.46
  • 4-hydroxyphenylpyruvate dioxygenase II
  • HMS
Gene Name
Not Available
UniProtKB Entry
O52791Swiss-Prot
Organism
Amycolatopsis orientalis
NCBI Taxonomy ID
31958
Amino acid sequence
>lcl|BSEQ0017333|4-hydroxymandelate synthase
MQNFEIDYVEMYVENLEVAAFSWVDKYAFAVAGTSRSADHRSIALRQGQVTLVLTEPTSD
RHPAAAYLQTHGDGVADIAMATSDVAAAYEAAVRAGAEAVRAPGQHSEAAVTTATIGGFG
DVVHTLIQRDGTSAELPPGFTGSMDVTNHGKGDVDLLGIDHFAICLNAGDLGPTVEYYER
ALGFRQIFDEHIVVGAQAMNSTVVQSASGAVTLTLIEPDRNADPGQIDEFLKDHQGAGVQ
HIAFNSNDAVRAVKALSERGVEFLKTPGAYYDLLGERITLQTHSLDDLRATNVLADEDHG
GQLFQIFTASTHPRHTIFFEVIERQGAGTFGSSNIKALYEAVELERTGQSEFGAARR
Number of residues
357
Molecular Weight
38338.19
Theoretical pI
4.59
GO Classification
Functions
4-hydroxymandelate synthase activity / 4-hydroxyphenylpyruvate dioxygenase activity / iron ion binding
Processes
aromatic amino acid family metabolic process / vancomycin biosynthetic process
General Function
Required to synthesize hydroxyphenylglycine, a recurring skeletal component of nonproteinogenic macrocyclic peptide antibiotics such as vancomycin. Catalyzes the conversion of p-hydroxyphenylpyruvate to p-hydroxymandelate. The decarboxylation and hydroxylation activities of HmaS show novel and distinct regioselectivity, compared to all other known p-hydroxyphenylpyruvate dioxygenases, by hydroxylating the benzylic position of the substrate instead of the phenyl ring.
Specific Function
4-hydroxymandelate synthase activity
Pfam Domain Function
Signal Regions
Not Available
Transmembrane Regions
Not Available
Cellular Location
Not Available
Gene sequence
>lcl|BSEQ0007846|1476 bp
ATGTCGGTCGAAGACTTCGATGTGGTTGTTGCTGGTGGCGGGCCTGCCGGTTCGACCGTG
GCCACCTTGGTGGCGATGCAGGGGCATCGGGTGCTGTTGCTGGAGAAAGAGGTCTTTCCC
CGGTACCAGATCGGTGAGTCGCTGCTGCCTGCCACGGTGCACGGGGTGTGCCGGATGCTC
GGCATCACGGACGAGCTGGCCAATGCCGGGTTCCCGGTGAAGCGGGGCGGCACTTTCCGC
TGGGGTGCGCGTCCGGAGCCGTGGACGTTCCACTTCGGTATCTCCGCCAAGATGGCGGGC
TCGACGTCGCACGCCTATCAGGTCGAGCGGGCGCGGTTCGACGAGATCTTGCTGAACAAC
GCCAAGCGCAAGGGCGTGGTCGTGCGGGAAGGGTCCCCGGTCACCGATGTGGTGGAAGAC
GGTGAGCGGGTCACCGGTCTGCGGTACACCGACGCCGATGGCAACGAGCGTGAAGTGTCA
GCGCGCTTCGTGATCGACGCGTCGGGCAACAAGAGCCGCCTCTACTCCAAGGTCGGCGGT
TCGCGGAACTACTCGGAGTTCTTCCGCAGCCTCGCGCTGTTCGGCTACTTCGAGGGTGGC
AAGCGGCTGCCCGCGCCGGTCTCGGGAAACATCCTGAGCGTTGCCTTCGACAGCGGCTGG
TTCTGGTACATCCCGCTGAGCGACACGCTGACCAGCGTCGGCGCGGTGGTGCGCCGGGAG
GACGCCGAGAAGATCCAGGGTGACCGGGAGAAGGCGCTCAACGCCCTGATCGCCGAGTGC
CCGCTGATCTCGGAGTACCTCGCGAACGCGACCAGGGTGACGACCGGCAAGTACGGGGAG
TTACGCGTCCGCAAGGACTACTCCTACCAGCAGGAGACCTACTGGCGGCCGGGGATGATC
CTGATCGGCGACGCCGCGTGCTTCGTGGACCCGGTGTTCTCGTCCGGTGTGCACCTGGCG
ACCTACAGCGCGCTGCTCGCGGCCCGGTCAATCAACAGCGTCCTGGCGGGCGATCTGGAC
GAGAAGACCGCACTGAACGAGTTCGAAATGCGGTATCGCCGCGAGTACGGGGTGTTCTAC
GAGTTCCTCGTGTCGTTCTATCAGATGAACGTGAATGAGGAGTCGTATTTCTGGCAGGCC
AAGAAGGTCACGCAGAACCAGAGCACCGATATCGAGTCGTTCGTCGAACTGATCGGTGGG
GTGTCGTCCGGTGAGACCGCGCTGACGGCCGCTGACCGGATCGCCGCGCGCAGTGCCGAA
TTCGCCGCGGCCGTGGACCAGATGGCCAGCGGCGACGGCGACAACATGGTGCCGATGTTC
AAGTCGACGGTGGTCAAGCAGGCGATGCAGGAAGCGGGCCAGGTCCAGATGAAGGCGCTG
CTCGGCGAGGACGCCGAACCCGAGCTGCCGCTGTTCCCCGGCGGCCTGGTGACCTCGCCC
GACGGAATGAAATGGCTGCCGCACCATCCGGCATGA
Chromosome Location
Not Available
Locus
Not Available
External Identifiers
ResourceLink
UniProtKB IDO52791
UniProtKB Entry NameHMAS_AMYOR
GenBank Protein ID2894184
GenBank Gene IDAJ223998
PDB ID(s)2R5V
General References
  1. van Wageningen AM, Kirkpatrick PN, Williams DH, Harris BR, Kershaw JK, Lennard NJ, Jones M, Jones SJ, Solenberg PJ: Sequencing and analysis of genes involved in the biosynthesis of a vancomycin group antibiotic. Chem Biol. 1998 Mar;5(3):155-62. [Article]
  2. Hubbard BK, Thomas MG, Walsh CT: Biosynthesis of L-p-hydroxyphenylglycine, a non-proteinogenic amino acid constituent of peptide antibiotics. Chem Biol. 2000 Dec;7(12):931-42. [Article]
  3. Brownlee J, He P, Moran GR, Harrison DH: Two roads diverged: the structure of hydroxymandelate synthase from Amycolatopsis orientalis in complex with 4-hydroxymandelate. Biochemistry. 2008 Feb 19;47(7):2002-13. doi: 10.1021/bi701438r. Epub 2008 Jan 24. [Article]

Associated Data

Drug Relations
DrugDrug groupPharmacological action?TypeActionsDetails
(2S)-hydroxy(4-hydroxyphenyl)ethanoic acidexperimentalunknowntargetDetails