4-hydroxymandelate synthase

Details

Name
4-hydroxymandelate synthase
Synonyms
  • 1.13.11.46
  • 4-hydroxyphenylpyruvate dioxygenase II
  • HMS
Gene Name
Not Available
Organism
Amycolatopsis orientalis
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
Iron ion binding
Specific 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.
Pfam Domain Function
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
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]

Drug Relations

Drug Relations
DrugBank IDNameDrug groupPharmacological action?ActionsDetails
DB07896(2S)-hydroxy(4-hydroxyphenyl)ethanoic acidexperimentalunknownDetails