The Primary Product of the Synthesis of Ascorbic Acid and its Analogues. Observations complementary to the preceding paper

Haworth, Walter Norman; Hirst, E. L.

doi:10.1002/hlca.19340170158

Cited by 13 publications

(3 citation statements)

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“…The well-known Kiliani-Fischer cyanohydrin synthesis (183, 310) of higher carbon sugars has been recently reviewed by Hudson (281). The Kiliani reaction has been applied by Haworth (253) and Reichstein (479) to the synthesis of Z-ascorbic acid (vitamin C) from Z-xylosone. The isolated intermediate in this case is thought to have a cyclic imino structure.…”

Section: Cn Ho Cnmentioning

confidence: 99%

The Preparation of Nitriles.

Mowry¹

1948

Chem. Rev.

392

103

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Section: Cn Ho Cnmentioning

confidence: 99%

The Preparation of Nitriles.

Mowry¹

1948

Chem. Rev.

392

103

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“…15 Chemical shifts derived from 1:!C NMR spectra of compounds 1, 2, and 4-6, determined in aqueous solution at the indicated pH, are given in Table I. It is evident that the C-3 chemical shifts noted for 1 and 4 are close to that observed for the ascorbate monoanion (6). Thus the presence of an anion at C-3 is indicated for both 1 and 4.…”

mentioning

confidence: 84%

Ascorbic acid derivatives. Structure determinations by carbon-13 nuclear magnetic resonance

Radford¹,

Sweeny²,

Iacobucci³

et al. 1979

J. Org. Chem.

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“…Investigations about biological oxidations and related topics in the first half of the twentieth century have permitted to discover the vitamin C. Among these pioneering works are considered the investigations conducted by Albert Szent-Giörgyi and other scientists ( Szent-Györgyi, 1928 ; King and Waugh, 1932 ; Hirst and Zilva, 1933 ; Hirst et al., 1933 ; Svirbely and Szent-Györgyi, 1933 ; Szent-Györgyi and Haworth, 1933 ; Szent-Gyoergyi, 1963 ), that together permitted to isolate and determine the chemical nature of the antiscorbutic factor, vitamin C. This compound was renamed L-ascorbic acid, which means “against scurvy”. When the molecular structure of AsA was elucidated, it was possible to develop chemical synthesis methods for its in vitro production ( Reichstein et al., 1933 ; Haworth and Hirst, 1934 ; Haworth et al., 1934 ; Reichstein and Grüssner, 1934 ). Thus, synthetic AsA was quickly and cheaply available.…”

Section: Introductionmentioning

confidence: 99%

Genetic and biochemical strategies for regulation of L-ascorbic acid biosynthesis in plants through the L-galactose pathway

Castro

Castro²,

Cobos³

2023

Front. Plant Sci.

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Vitamin C (L-ascorbic acid, AsA) is an essential compound with pleiotropic functions in many organisms. Since its isolation in the last century, AsA has attracted the attention of the scientific community, allowing the discovery of the L-galactose pathway, which is the main pathway for AsA biosynthesis in plants. Thus, the aim of this review is to analyze the genetic and biochemical strategies employed by plant cells for regulating AsA biosynthesis through the L-galactose pathway. In this pathway, participates eight enzymes encoded by the genes PMI, PMM, GMP, GME, GGP, GPP, GDH, and GLDH. All these genes and their encoded enzymes have been well characterized, demonstrating their participation in AsA biosynthesis. Also, have described some genetic and biochemical strategies that allow its regulation. The genetic strategy includes regulation at transcriptional and post-transcriptional levels. In the first one, it was demonstrated that the expression levels of the genes correlate directly with AsA content in the tissues/organs of the plants. Also, it was proved that these genes are light-induced because they have light-responsive promoter motifs (e.g., ATC, I-box, GT1 motif, etc.). In addition, were identified some transcription factors that function as activators (e.g., SlICE1, AtERF98, SlHZ24, etc.) or inactivators (e.g., SlL1L4, ABI4, SlNYYA10) regulate the transcription of these genes. In the second one, it was proved that some genes have alternative splicing events and could be a mechanism to control AsA biosynthesis. Also, it was demonstrated that a conserved cis-acting upstream open reading frame (5’-uORF) located in the 5’-untranslated region of the GGP gene induces its post-transcriptional repression. Among the biochemical strategies discovered is the control of the enzyme levels (usually by decreasing their quantities), control of the enzyme catalytic activity (by increasing or decreasing its activity), feedback inhibition of some enzymes (GME and GGP), subcellular compartmentation of AsA, the metabolon assembly of the enzymes, and control of AsA biosynthesis by electron flow. Together, the construction of this basic knowledge has been establishing the foundations for generating genetically improved varieties of fruits and vegetables enriched with AsA, commonly used in animal and human feed.

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The Primary Product of the Synthesis of Ascorbic Acid and its Analogues. Observations complementary to the preceding paper

Cited by 13 publications

References 0 publications

The Preparation of Nitriles.

The Preparation of Nitriles.

Ascorbic acid derivatives. Structure determinations by carbon-13 nuclear magnetic resonance

Genetic and biochemical strategies for regulation of L-ascorbic acid biosynthesis in plants through the L-galactose pathway

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