Pantothenic Acid. IV. Formation of β-Alanine by Cleavage

Weinstock, Harry H.; Mitchell, Herschel K.; Pratt, Ernest F.; Williams, Roger J.

doi:10.1021/ja01875a029

Cited by 45 publications

(16 citation statements)

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“…Other n ‐ω amino acids, β‐ala, γ‐ABA, and δ‐AVA, exist mostly in bound form ranging from 73% to 90% and are nonproteinogenic, although they do occur in the biosphere (Weinstock et al. ; Syrjanen et al. ; Owens and Kriegstein ).…”

Section: Resultsmentioning

confidence: 99%

A search for amino acids and nucleobases in the Martian meteorite Roberts Massif 04262 using liquid chromatography‐mass spectrometry

Callahan

Burton

Elsila

et al. 2013

Meteorit & Planetary Scien

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Abstract-The investigation into whether Mars contains signatures of past or present life is of great interest to science and society. Amino acids and nucleobases are compounds that are essential for all known life on Earth and are excellent target molecules in the search for potential Martian biomarkers or prebiotic chemistry. Martian meteorites represent the only samples from Mars that can be studied directly in the laboratory on Earth. Here, we analyzed the amino acid and nucleobase content of the shergottite Roberts Massif (RBT) 04262 using liquid chromatography-mass spectrometry. We did not detect any nucleobases above our detection limit in formic acid extracts; however, we did measure a suite of protein and nonprotein amino acids in hot-water extracts with high relative abundances of b-alanine and c-amino-n-butyric acid. The presence of only low (to absent) levels of several proteinogenic amino acids and a lack of nucleobases suggest that this meteorite fragment is fairly uncontaminated with respect to these common biological compounds. The distribution of straight-chained amine-terminal n-x-amino acids in RBT 04262 resembled those previously measured in thermally altered carbonaceous meteorites Chan et al. 2012). A carbon isotope ratio of À24& AE 6& for b-alanine in RBT 04262 is in the range of reduced organic carbon previously measured in Martian meteorites (Steele et al. 2012). The presence of n-x-amino acids may be due to a high temperature Fischer-Tropschtype synthesis during igneous processing on Mars or impact ejection of the meteorites from Mars, but more experimental data are needed to support these hypotheses.

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Section: Resultsmentioning

confidence: 99%

A search for amino acids and nucleobases in the Martian meteorite Roberts Massif 04262 using liquid chromatography‐mass spectrometry

Callahan

Burton

Elsila

et al. 2013

Meteorit & Planetary Scien

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“…Subsequently, Lochhead & Landerkin (1942) reported that pantothenic acid also stimulated the growth of several species of osmophilic yeast. For some yeast, β‐alanine, the precursor of pantothenic acid, could replace pantothenic acid as a growth factor (Williams & Rohrman, 1936; Weinstock et al ., 1939; Williams et al ., 1940; Lochhead & Landerkin, 1942; Sarett & Cheldelin, 1945a), consistent with at least some yeast being capable of pantothenic acid biosynthesis from β‐alanine.…”

Section: Pantothenic Acid and The Biosynthesis Of Coenzyme A (Coa)mentioning

confidence: 99%

Coenzyme A biosynthesis: an antimicrobial drug target

Spry¹,

Kirk²,

Saliba³

2008

FEMS Microbiol Rev

241

260

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Pantothenic acid, a precursor of coenzyme A (CoA), is essential for the growth of pathogenic microorganisms. Since the structure of pantothenic acid was determined, many analogues of this essential metabolite have been prepared. Several have been demonstrated to exert an antimicrobial effect against a range of microorganisms by inhibiting the utilization of pantothenic acid, validating pantothenic acid utilization as a potential novel antimicrobial drug target. This review commences with an overview of the mechanisms by which various microorganisms acquire the pantothenic acid they require for growth, and the universal CoA biosynthesis pathway by which pantothenic acid is converted into CoA. A detailed survey of studies that have investigated the inhibitory activity of analogues of pantothenic acid and other precursors of CoA follows. The potential of inhibitors of both pantothenic acid utilization and biosynthesis as novel antibacterial, antifungal and antimalarial agents is discussed, focusing on inhibitors and substrates of pantothenate kinase, the enzyme catalysing the rate-limiting step of CoA biosynthesis in many organisms. The best strategies are considered for identifying inhibitors of pantothenic acid utilization and biosynthesis that are potent and selective inhibitors of microbial growth and that may be suitable for use as chemotherapeutic agents in humans.

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“…(1939). This (on the basis of the /?-alanine yields, Weinstock et al 1939) was adjudged to be not more than 90% pure. Its impurity was later further shown by the fact that whereas its analysis led to the molecular formula (for the calcium salt) of (C8HI4O6N)&a, the correct formula is (C,H,,06N),Ca (R.J.W.…”

Section: Plant Tissues (Koglmentioning

confidence: 96%