Model Compounds for Protein-Nucleic Acid Interactions. 5.la 5-S-Cysteinyluracil Monohydrate, a Photoaddition Product between an Amino Acid and Pyrimidine Base

Graheme J.B. Williams; A. J. Varghese; Helen M. Berman

doi:10.1021/ja00451a047

Model Compounds for Protein-Nucleic Acid Interactions. 5.la 5-S-Cysteinyluracil Monohydrate, a Photoaddition Product between an Amino Acid and Pyrimidine Base

Graheme J.B. Williams, A. J. Varghese, Helen M. Berman

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

The molecular and crystal structure of a pyrimidine-amino acid irradiation product, 5-S-cysteinyluridine, has been determined by x-ray crystallography. The cell dimensions are a = 14.59 (3) Å, b = 6.82 (1) Å, β = 95.1 (1)°, space group P2₁ with two formula units of C₇H₉N₃O₄S-H₂O per cell. The pyrimidine rings are linked together in ribbons by four hydrogen bonds. Seven other hydrogen bonds interconnect the other polar functions and indicate how the unusual conformation of the cysteinyl group is stabilized. The irradiation product in its observed conformation can be fit into a RNA helix and proposed structures of intermediates in the in vivo covalent coupling of cysteine to uracil are described.

Original language	American English
Pages (from-to)	3150-3154
Number of pages	5
Journal	Journal of the American Chemical Society
Volume	99
Issue number	9
DOIs	https://doi.org/10.1021/ja00451a047
State	Published - 1977
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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title = "Model Compounds for Protein-Nucleic Acid Interactions. 5.la 5-S-Cysteinyluracil Monohydrate, a Photoaddition Product between an Amino Acid and Pyrimidine Base",

abstract = "The molecular and crystal structure of a pyrimidine-amino acid irradiation product, 5-S-cysteinyluridine, has been determined by x-ray crystallography. The cell dimensions are a = 14.59 (3) {\AA}, b = 6.82 (1) {\AA}, β = 95.1 (1)°, space group P21 with two formula units of C7H9N3O4S-H2O per cell. The pyrimidine rings are linked together in ribbons by four hydrogen bonds. Seven other hydrogen bonds interconnect the other polar functions and indicate how the unusual conformation of the cysteinyl group is stabilized. The irradiation product in its observed conformation can be fit into a RNA helix and proposed structures of intermediates in the in vivo covalent coupling of cysteine to uracil are described.",

author = "Williams, {Graheme J.B.} and Varghese, {A. J.} and Berman, {Helen M.}",

year = "1977",

doi = "10.1021/ja00451a047",

language = "American English",

volume = "99",

pages = "3150--3154",

journal = "Journal of the American Chemical Society",

issn = "0002-7863",

publisher = "American Chemical Society",

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T1 - Model Compounds for Protein-Nucleic Acid Interactions. 5.la 5-S-Cysteinyluracil Monohydrate, a Photoaddition Product between an Amino Acid and Pyrimidine Base

AU - Williams, Graheme J.B.

AU - Varghese, A. J.

AU - Berman, Helen M.

PY - 1977

Y1 - 1977

N2 - The molecular and crystal structure of a pyrimidine-amino acid irradiation product, 5-S-cysteinyluridine, has been determined by x-ray crystallography. The cell dimensions are a = 14.59 (3) Å, b = 6.82 (1) Å, β = 95.1 (1)°, space group P21 with two formula units of C7H9N3O4S-H2O per cell. The pyrimidine rings are linked together in ribbons by four hydrogen bonds. Seven other hydrogen bonds interconnect the other polar functions and indicate how the unusual conformation of the cysteinyl group is stabilized. The irradiation product in its observed conformation can be fit into a RNA helix and proposed structures of intermediates in the in vivo covalent coupling of cysteine to uracil are described.

AB - The molecular and crystal structure of a pyrimidine-amino acid irradiation product, 5-S-cysteinyluridine, has been determined by x-ray crystallography. The cell dimensions are a = 14.59 (3) Å, b = 6.82 (1) Å, β = 95.1 (1)°, space group P21 with two formula units of C7H9N3O4S-H2O per cell. The pyrimidine rings are linked together in ribbons by four hydrogen bonds. Seven other hydrogen bonds interconnect the other polar functions and indicate how the unusual conformation of the cysteinyl group is stabilized. The irradiation product in its observed conformation can be fit into a RNA helix and proposed structures of intermediates in the in vivo covalent coupling of cysteine to uracil are described.

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Model Compounds for Protein-Nucleic Acid Interactions. 5.la 5-S-Cysteinyluracil Monohydrate, a Photoaddition Product between an Amino Acid and Pyrimidine Base

Abstract

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