Structure of a pyrimidine amino acid from pea seedlings

Brown, Eric G.; Mangat, B. S.

doi:10.1016/0304-4165(69)90305-5

Cited by 22 publications

(3 citation statements)

References 12 publications

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“…Previous work with pea seedlings (Brown & Silver, 1966; Silver & Gilmore, 1969) had indicated that GMP stimulated the production of a uracilylalanine, now known to be isowillardiine (Brown & Mangat, 1969), but this could not be reproduced in the present studies and is believed to have been attributable to a generalized response by seeds suffering from a nutritional deficiency. A contemporary batch of pea seeds from the previous source were found to exhibit 'marsh spot' (a Mn2+-deficiency resulting in atro-Vol.…”

Section: Effect Ofuracil and Related Compounds On Formation Of Willarcontrasting

confidence: 69%

“…Three contiguous peaks were recorded (fractions 65-71, 71-78 and 78-86). By using the chromatographic, electrophoretic and spectrophotometric methods described previously (Brown & Silver, 1966;Brown & Mangat, 1969), comparisons with authentic samples showed that peak (1) consisted largely of willardiine, peak (2) of isowillardiine and peak (3) of ,-(isoxazolin-5-oxo-2-yl)alanine (Lambein et al, 1969). For routine extraction of willardiine and isowillardiine, peaks (1) and (2) were separately evaporated in vacuo and sequentially chromatographed on Whatman no.…”

Section: Methodsmentioning

confidence: 99%

“…Subsequent n.m.r. and mass-spectrometric studies (Brown & Mangat, 1969) necessitated revision of this structure, reassigning the alanine side chain to N-3 of the pyrimidine ring to give f4-(2,4dihydroxypyrimidin-3-yl)alanine (II). Concurrently but independently, Lambein & Van Parijs (1968) deduced formula (II) for a compound they had also isolated from pea seedlings.…”

mentioning

confidence: 99%

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Biosynthesis of willardiine and isowillardiine in germinating pea seeds and seedlings

Ashworth

Brown

Roberts

1972

Biochemical Journal

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The synthesis of the pyrimidinyl amino acids willardiine and isowillardiine was studied in vivo and in vitro. Uracil derivatives stimulate the biosynthesis of both compounds; the free base is the most effective. Significant incorporation of [2-(14)C]uracil and [6-(14)C]orotate into willardiine and isowillardiine was found. Incorporation of [6-(14)C]orotate was substantially decreased in the presence of uracil, and to a lesser extent by uridine and UMP. [3-(14)C]Serine was incorporated into the alanine side chain of the two uracilylalanines but not into the ring. The effect of a number of uracil analogues and inhibitors of pyrimidine metabolism was examined. Some were shown to stimulate the biosynthesis; the most noticeable effects were obtained with 6-azauracil and 2-thiouracil. Attempts to obtain extracts capable of synthesizing the uracilylalanines from uracil and serine were unsuccessful, but weak activity was observed when serine was replaced by O-acetylserine.

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Section: Effect Ofuracil and Related Compounds On Formation Of Willarcontrasting

confidence: 69%

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

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Biosynthesis of willardiine and isowillardiine in germinating pea seeds and seedlings

Ashworth

Brown

Roberts

1972

Biochemical Journal

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Preparation and mass spectral characterization of pentafluorobenzyl derivatives of alkyl and hydroxyalkyl-nucleobase DNA adducts

Saha

Kresbach

Giese

et al. 1989

Biol. Mass Spectrom.

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Pentafluorobenzyl (PFBz) derivatives of the following nucleobases were prepared: cytosine, 5-methylcytosine, O2-methylcytosine, O2-ethylthymine, O4-ethylthymine, 5-hydroxymethyluracil, N6-methyladenine, O6-methylguanine, O6-hydroxyethylguanine and O6-hydroxyethylpurine. 13C nuclear magnetic resonance was diagnostic for O- versus N-attachment of the PFBz moiety: the resonance of the methylene carbon appeared in the range 29.15-42.13 ppm for NCH2C6F5, and 58.45-69.01 for OCH2C6F5. Considerable structural information was provided by mass spectrometry with ionization by electron impact. All of the derivatives were detected with high sensitivity and specificity by gas chromatography with detection by electron capture negative ion mass spectrometry, reflecting not only their chemical and physical stability, but also their strong tendency to form a structurally diagnostic anion, [M - PFBz]-, in high yield under these ionization conditions. PFBz derivatives are therefore attractive forms of alkyl-substituted nucleobases for analysis by mass spectrometry.

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Amino Acids Bound to DNA

Balis

1976

Aging, Carcinogenesis, and Radiation Biology

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Structure of a pyrimidine amino acid from pea seedlings

Cited by 22 publications

References 12 publications

Biosynthesis of willardiine and isowillardiine in germinating pea seeds and seedlings

Biosynthesis of willardiine and isowillardiine in germinating pea seeds and seedlings

Preparation and mass spectral characterization of pentafluorobenzyl derivatives of alkyl and hydroxyalkyl-nucleobase DNA adducts

Amino Acids Bound to DNA

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