DOI: 10.1111/j.1432-1033.1981.tb06299.x. Syntheses of <scp>l</scp>‐Tyrosine‐Related Amino Acids by Tyrosine Phenol‐lyase of <i>Citrobacter intermedius</i>

Syntheses of l‐Tyrosine‐Related Amino Acids by Tyrosine Phenol‐lyase of Citrobacter intermedius

10.1111/j.1432-1033.1981.tb06299.x

Crossref journal-article

Wiley

European Journal of Biochemistry (311)

Abstract

Degradation of tyrosine to phenol, pyruvate and ammonia by tyrosine phenol‐lyase from Citrobacter intermedius (formerly named Escherichia intermedia) is readily reversible at high concentrations of pyruvate and ammonia. Spectrophotometric studies indicate that ammonia is the first substrate which interacts with bound pyridoxal 5′‐phosphate. Kinetic results show that pyruvate is the second substrate bound, hence phenol must be the third. When an appropriate phenol derivative is substituted for phenol, the corresponding tyrosine analogue can be synthesized. 3‐Fluoro‐, 2‐fluoro‐, 3‐chloro‐, 2‐chloro‐, 3‐bromo‐, 2‐bromo‐, 2‐iodo‐, 3‐methyl‐, 2‐methyl and 2‐methoxy‐l‐tyrosines have been synthesized by this reaction. By using various phenol derivatives or tyrosine analogues as substrates, the substrate specificity of tyrosine phenol‐lyase is investigated, and the situation of its active site is discussed.

Bibliography

NAGASAWA, T., UTAGAWA, T., GOTO, J., KIM, C., TANI, Y., KUMAGAI, H., & YAMADA, H. (1981). Syntheses of lâTyrosineâRelated Amino Acids by Tyrosine Phenolâlyase of Citrobacter intermedius. European Journal of Biochemistry, 117(1), 33â40. Portico.

Authors 7

Toru NAGASAWA (first)
Takashi UTAGAWA (additional)
Joji GOTO (additional)
Chan‐Jo KIM (additional)
Yoshiki TANI (additional)
Hidehiko KUMAGAI (additional)
Hideaki YAMADA (additional)

References 21 Referenced 68

{'key': 'e_1_2_3_2_2', 'first-page': '497', 'volume': '3', 'author': 'Kakihara Y.', 'year': '1953', 'journal-title': 'Med. J. Osaka Univ.'} / Med. J. Osaka Univ. by Kakihara Y. (1953)
{'key': 'e_1_2_3_3_2', 'first-page': '509', 'volume': '3', 'author': 'Uchida M.', 'year': '1953', 'journal-title': 'Med. J. Osaka Univ.'} / Med. J. Osaka Univ. by Uchida M. (1953)
{'key': 'e_1_2_3_4_2', 'first-page': '727', 'volume': '9', 'author': 'Yoshimatsu H.', 'year': '1957', 'journal-title': 'Med. J. Osaka Univ.'} / Med. J. Osaka Univ. by Yoshimatsu H. (1957)
10.1016/0003-9861(65)90002-0
10.1016/0006-291X(68)90246-5 / Biochem. Biophys. Res. Commun. by S. Yamada H. (1968)
10.1016/S0021-9258(19)77158-0
10.1016/S0021-9258(19)77159-2
10.1016/0006-291X(69)90826-2
{'key': 'e_1_2_3_10_2', 'first-page': '476', 'volume': '205', 'author': 'Ueno T.', 'year': '1970', 'journal-title': 'Biochem. Biophys. Acta'} / Biochem. Biophys. Acta by Ueno T. (1970)
10.1016/0006-291X(70)90393-1
10.1016/S0006-291X(72)80148-7
10.1016/S0021-9258(19)41744-4 / J. Biol. Chem. by Kumagai H. (1975)
10.1016/S0021-9258(19)52451-6
10.1021/ja01318a036
10.1016/0926-6569(63)90211-6
{'key': 'e_1_2_3_17_2', 'first-page': '13', 'volume-title': 'The Enzymes', 'author': 'Cleland W. W.', 'year': '1970'} / The Enzymes by Cleland W. W. (1970)
10.1021/ja01567a087 / J. Am. Chem. Soc. by Jenkins W. T. (1957)
10.1016/S0021-9258(18)64252-8 / J. Biol. Chem. by Jenkins W. T. (1961)
10.1016/S0021-9258(18)72397-1
10.1016/S0021-9258(19)76857-4 / J. Biol. Chem. by Shukuya R. (1953)
{'key': 'e_1_2_3_22_2', 'first-page': '633', 'volume': '84', 'author': 'Muro T.', 'year': '1978', 'journal-title': 'Agric. Biol. Chem.'} / Agric. Biol. Chem. by Muro T. (1978)

Dates

Type	When
Created	15 years, 1 month ago (July 21, 2010, 1:03 p.m.)
Deposited	1 year, 9 months ago (Nov. 23, 2023, 1:36 a.m.)
Indexed	4 weeks, 2 days ago (July 30, 2025, 9:54 a.m.)
Issued	44 years, 2 months ago (June 1, 1981)
Published	44 years, 2 months ago (June 1, 1981)
Published Online	20 years, 5 months ago (March 3, 2005)
Published Print	44 years, 2 months ago (June 1, 1981)

Funders 0

None

BibTeX

@article{NAGASAWA_1981, title={Syntheses of <scp>l</scp>‐Tyrosine‐Related Amino Acids by Tyrosine Phenol‐lyase of Citrobacter intermedius}, volume={117}, ISSN={1432-1033}, url={http://dx.doi.org/10.1111/j.1432-1033.1981.tb06299.x}, DOI={10.1111/j.1432-1033.1981.tb06299.x}, number={1}, journal={European Journal of Biochemistry}, publisher={Wiley}, author={NAGASAWA, Toru and UTAGAWA, Takashi and GOTO, Joji and KIM, Chan‐Jo and TANI, Yoshiki and KUMAGAI, Hidehiko and YAMADA, Hideaki}, year={1981}, month=jun, pages={33–40} }

JSON

{
  "indexed": {
    "date-parts": [
      [
        2025,
        7,
        30
      ]
    ],
    "date-time": "2025-07-30T13:54:00Z",
    "timestamp": 1753883640815
  },
  "reference-count": 21,
  "publisher": "Wiley",
  "issue": "1",
  "license": [
    {
      "start": {
        "date-parts": [
          [
            2005,
            3,
            3
          ]
        ],
        "date-time": "2005-03-03T00:00:00Z",
        "timestamp": 1109808000000
      },
      "content-version": "vor",
      "delay-in-days": 8676,
      "URL": "http://onlinelibrary.wiley.com/termsAndConditions#vor"
    }
  ],
  "content-domain": {
    "domain": [],
    "crossmark-restriction": false
  },
  "published-print": {
    "date-parts": [
      [
        1981,
        6
      ]
    ]
  },
  "abstract": "<jats:p>Degradation of tyrosine to phenol, pyruvate and ammonia by tyrosine phenol\u2010lyase from <jats:italic>Citrobacter intermedius</jats:italic> (formerly named <jats:italic>Escherichia intermedia</jats:italic>) is readily reversible at high concentrations of pyruvate and ammonia. Spectrophotometric studies indicate that ammonia is the first substrate which interacts with bound pyridoxal 5\u2032\u2010phosphate. Kinetic results show that pyruvate is the second substrate bound, hence phenol must be the third. When an appropriate phenol derivative is substituted for phenol, the corresponding tyrosine analogue can be synthesized. 3\u2010Fluoro\u2010, 2\u2010fluoro\u2010, 3\u2010chloro\u2010, 2\u2010chloro\u2010, 3\u2010bromo\u2010, 2\u2010bromo\u2010, 2\u2010iodo\u2010, 3\u2010methyl\u2010, 2\u2010methyl and 2\u2010methoxy\u2010<jats:sc>l</jats:sc>\u2010tyrosines have been synthesized by this reaction. By using various phenol derivatives or tyrosine analogues as substrates, the substrate specificity of tyrosine phenol\u2010lyase is investigated, and the situation of its active site is discussed.</jats:p>",
  "DOI": "10.1111/j.1432-1033.1981.tb06299.x",
  "type": "journal-article",
  "created": {
    "date-parts": [
      [
        2010,
        7,
        21
      ]
    ],
    "date-time": "2010-07-21T17:03:56Z",
    "timestamp": 1279731836000
  },
  "page": "33-40",
  "source": "Crossref",
  "is-referenced-by-count": 68,
  "title": "Syntheses of <scp>l</scp>\u2010Tyrosine\u2010Related Amino Acids by Tyrosine Phenol\u2010lyase of <i>Citrobacter intermedius</i>",
  "prefix": "10.1111",
  "volume": "117",
  "author": [
    {
      "given": "Toru",
      "family": "NAGASAWA",
      "sequence": "first",
      "affiliation": []
    },
    {
      "given": "Takashi",
      "family": "UTAGAWA",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Joji",
      "family": "GOTO",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Chan\u2010Jo",
      "family": "KIM",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Yoshiki",
      "family": "TANI",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Hidehiko",
      "family": "KUMAGAI",
      "sequence": "additional",
      "affiliation": []
    },
    {
      "given": "Hideaki",
      "family": "YAMADA",
      "sequence": "additional",
      "affiliation": []
    }
  ],
  "member": "311",
  "published-online": {
    "date-parts": [
      [
        2005,
        3,
        3
      ]
    ]
  },
  "reference": [
    {
      "key": "e_1_2_3_2_2",
      "first-page": "497",
      "volume": "3",
      "author": "Kakihara Y.",
      "year": "1953",
      "journal-title": "Med. J. Osaka Univ."
    },
    {
      "key": "e_1_2_3_3_2",
      "first-page": "509",
      "volume": "3",
      "author": "Uchida M.",
      "year": "1953",
      "journal-title": "Med. J. Osaka Univ."
    },
    {
      "key": "e_1_2_3_4_2",
      "first-page": "727",
      "volume": "9",
      "author": "Yoshimatsu H.",
      "year": "1957",
      "journal-title": "Med. J. Osaka Univ."
    },
    {
      "key": "e_1_2_3_5_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0003-9861(65)90002-0"
    },
    {
      "key": "e_1_2_3_6_2",
      "doi-asserted-by": "crossref",
      "first-page": "10",
      "DOI": "10.1016/0006-291X(68)90246-5",
      "volume": "33",
      "author": "S. Yamada H.",
      "year": "1968",
      "journal-title": "Biochem. Biophys. Res. Commun."
    },
    {
      "key": "e_1_2_3_7_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0021-9258(19)77158-0"
    },
    {
      "key": "e_1_2_3_8_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0021-9258(19)77159-2"
    },
    {
      "key": "e_1_2_3_9_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0006-291X(69)90826-2"
    },
    {
      "key": "e_1_2_3_10_2",
      "first-page": "476",
      "volume": "205",
      "author": "Ueno T.",
      "year": "1970",
      "journal-title": "Biochem. Biophys. Acta"
    },
    {
      "key": "e_1_2_3_11_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0006-291X(70)90393-1"
    },
    {
      "key": "e_1_2_3_12_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0006-291X(72)80148-7"
    },
    {
      "key": "e_1_2_3_13_2",
      "doi-asserted-by": "crossref",
      "first-page": "1661",
      "DOI": "10.1016/S0021-9258(19)41744-4",
      "volume": "250",
      "author": "Kumagai H.",
      "year": "1975",
      "journal-title": "J. Biol. Chem."
    },
    {
      "key": "e_1_2_3_14_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0021-9258(19)52451-6"
    },
    {
      "key": "e_1_2_3_15_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1021/ja01318a036"
    },
    {
      "key": "e_1_2_3_16_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/0926-6569(63)90211-6"
    },
    {
      "key": "e_1_2_3_17_2",
      "first-page": "13",
      "volume-title": "The Enzymes",
      "author": "Cleland W. W.",
      "year": "1970"
    },
    {
      "key": "e_1_2_3_18_2",
      "doi-asserted-by": "crossref",
      "first-page": "2656",
      "DOI": "10.1021/ja01567a087",
      "volume": "79",
      "author": "Jenkins W. T.",
      "year": "1957",
      "journal-title": "J. Am. Chem. Soc."
    },
    {
      "key": "e_1_2_3_19_2",
      "doi-asserted-by": "crossref",
      "first-page": "1121",
      "DOI": "10.1016/S0021-9258(18)64252-8",
      "volume": "234",
      "author": "Jenkins W. T.",
      "year": "1961",
      "journal-title": "J. Biol. Chem."
    },
    {
      "key": "e_1_2_3_20_2",
      "doi-asserted-by": "publisher",
      "DOI": "10.1016/S0021-9258(18)72397-1"
    },
    {
      "key": "e_1_2_3_21_2",
      "doi-asserted-by": "crossref",
      "first-page": "1653",
      "DOI": "10.1016/S0021-9258(19)76857-4",
      "volume": "235",
      "author": "Shukuya R.",
      "year": "1953",
      "journal-title": "J. Biol. Chem."
    },
    {
      "key": "e_1_2_3_22_2",
      "first-page": "633",
      "volume": "84",
      "author": "Muro T.",
      "year": "1978",
      "journal-title": "Agric. Biol. Chem."
    }
  ],
  "container-title": "European Journal of Biochemistry",
  "original-title": [],
  "language": "en",
  "link": [
    {
      "URL": "https://api.wiley.com/onlinelibrary/tdm/v1/articles/10.1111%2Fj.1432-1033.1981.tb06299.x",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "text-mining"
    },
    {
      "URL": "https://febs.onlinelibrary.wiley.com/doi/pdf/10.1111/j.1432-1033.1981.tb06299.x",
      "content-type": "unspecified",
      "content-version": "vor",
      "intended-application": "similarity-checking"
    }
  ],
  "deposited": {
    "date-parts": [
      [
        2023,
        11,
        23
      ]
    ],
    "date-time": "2023-11-23T06:36:56Z",
    "timestamp": 1700721416000
  },
  "score": 1,
  "resource": {
    "primary": {
      "URL": "https://febs.onlinelibrary.wiley.com/doi/10.1111/j.1432-1033.1981.tb06299.x"
    }
  },
  "subtitle": [],
  "short-title": [],
  "issued": {
    "date-parts": [
      [
        1981,
        6
      ]
    ]
  },
  "references-count": 21,
  "journal-issue": {
    "issue": "1",
    "published-print": {
      "date-parts": [
        [
          1981,
          6
        ]
      ]
    }
  },
  "alternative-id": [
    "10.1111/j.1432-1033.1981.tb06299.x"
  ],
  "URL": "http://dx.doi.org/10.1111/j.1432-1033.1981.tb06299.x",
  "relation": {},
  "ISSN": [
    "0014-2956",
    "1432-1033"
  ],
  "subject": [],
  "container-title-short": "European Journal of Biochemistry",
  "published": {
    "date-parts": [
      [
        1981,
        6
      ]
    ]
  }
}