Pantothenic acid derivatives

The pantothenic acid derivatives include pantothenic acid (BAN), pantothenol (BAN), dexpanthenol (rINN), and hopantenic acid (rINN). 

CAS 16816-67-4. C H b OjS.,. The disulfide form of A-pantothenylthioethanolamine. Lactobacilus bulgaricus growth factor (LBF). A fragment of coenzyme A, a pantothenic acid derivative. 

Chem. Soc. 60, 2719 (1938). Pantothenic acid derivs sold commercially are prepd by synthesis. May be prepd by the direct condensation of d-alanine with the optically resolved form of the lactone of pantoic acid (2,4-dihydroxy-3,3-di-... 

Lipmann, F., Kaplan, N.O. Novelli, G.D, Tuttle, L.C., and Guirard, B.M., 1947. Coenzyme for acetylation, a pantothenic acid derivative. Journal of Biological Chemistry. 167 869. 

The complete structure of CoA is now established. The coenzyme is a pantothenic acid derivative in which the vitamin is doubly bound and is liberated by the combined action of two enzymes, an intestinal phosphatase and an unidentified peptidase from avian liver. The latter enzyme has recently been found in fresh extracts of hog kidney... 

Alternatively, the derivatization was conducted using either thionyl chloride or n-butylboronic acid instead of trifluoroacetic anhydride. The resolution factors between the D-pantothenic acid and L-pantothenic acid derivatives were 1.6 (trifluoroacetates), 1.16 (cyclic sulflnates Fig. 32), and 1.55 (cyclic boronates Fig. 33), respectively. Although all were sufficiently high, trifluoroacetylation resulted in the best resolution factor. The sulfinates have two chiral centers in their molecules, but the respective chromatogram showed the separation of only one pair of enantiomers (80,81). 

In recognition of its wide distribution in foods, the name pantothenic acid, derived from the Greek word pantothen— meaning everywhere, was first given to it in 1933, by R. J. Williams, then of Oregon State, later at the University of Texas. 

Administration of pantothenic acid orally and application of pantothenol ointment to the skin have been shown to promote wound healing in animals. However, few data exist in humans to support these findings. A pantothenic acid derivative called pantethine has been reported to have a cholesterol lowering effect. 

Table 1. Physical Properties of Pantothenic Acid and Derivatives...

Certain amino acids and their derivatives, although not found in proteins, nonetheless are biochemically important. A few of the more notable examples are shown in Figure 4.5. y-Aminobutyric acid, or GABA, is produced by the decarboxylation of glutamic acid and is a potent neurotransmitter. Histamine, which is synthesized by decarboxylation of histidine, and serotonin, which is derived from tryptophan, similarly function as neurotransmitters and regulators. /3-Alanine is found in nature in the peptides carnosine and anserine and is a component of pantothenic acid (a vitamin), which is a part of coenzyme A. Epinephrine (also known as adrenaline), derived from tyrosine, is an important hormone. Penicillamine is a constituent of the penicillin antibiotics. Ornithine, betaine, homocysteine, and homoserine are important metabolic intermediates. Citrulline is the immediate precursor of arginine. 

Pantothenic acid is found in extracts from nearly all plants, bacteria, and animals, and the name derives from the Greek pantos, meaning everywhere. It is required in the diet of all vertebrates, but some microorganisms produce it in the rumens of animals such as cattle and sheep. This vitamin is widely distributed in foods common to the human diet, and deficiencies are only observed in cases of severe malnutrition. The eminent German-born biochemist Fritz Lipmann was the first to show that a coenzyme was required to facilitate biological acetylation reactions. (The A in... 

The hydrogenation of ketones with O or N functions in the a- or / -position is accomplished by several rhodium compounds [46 a, b, e, g, i, j, m, 56], Many of these examples have been applied in the synthesis of biologically active chiral products [59]. One of the first examples was the asymmetric synthesis of pantothenic acid, a member of the B complex vitamins and an important constituent of coenzyme A. Ojima et al. first described this synthesis in 1978, the most significant step being the enantioselective reduction of a cyclic a-keto ester, dihydro-4,4-dimethyl-2,3-furandione, to D-(-)-pantoyl lactone. A rhodium complex derived from [RhCl(COD)]2 and the chiral pyrrolidino diphosphine, (2S,4S)-N-tert-butoxy-carbonyl-4-diphenylphosphino-2-diphenylphosphinomethyl-pyrrolidine ((S, S) -... 

Note that this overall reaction requires three coenzymes that we encountered as metabolites of vitamins in chapter 15 NAD+, derived from lucotiiuc acid or nicotinamide FAD, derived from riboflavin and coenzyme A(CoASH), derived from pantothenic acid. In the overall process, acetyl-SCoA is oxidized to two molecules of carbon dioxide with the release of CoASH. Both NAD+ and FAD are reduced to, respectively, NADH and FADH2. Note that one molecule of guanosine triphosphate, GTP, functionally equivalent to ATP, is generated in the process. 

Coenzyme A a derivative of pantothenic acid required for many reactions in human metabolism. 

Metabolic derivatives of pantothenic acid are of fundamental importance in acyl transfer reactions and in condensation reactions requiring an acidic a-proton. The... 

Glycine max (L.) Merrill G. soja Sieb. Zucc. Da Dou Ye Da Dou (Soybean) (seed) Protein, isoflavone derivatives, genisteine, daidzein, riboflavin, thiamine, niacin, pantothenic acid, choline.33,67 Phytoestrogenic, elevate the vasomotor system, prevent cancer, a potent inhibitor of protein tyrosine kinase. 

The B-group is a heterogeneous collection of water-soluble vitamins, most of which function as co-enzymes or are precursors of co-enzymes. The B-group vitamins are thiamin, riboflavin, niacin, biotin, pantothenic acid, pyridoxine (and related substances, vitamin B6), folate and cobalamin (and its derivatives, vitamin B12). 

Pantothenic acid (6.25) is a dimethyl derivative of butyric acid linked to / -alanine. Pantothenate is part of the structure of co-enzyme A (CoA), and... 

Some enzymes associate with a nonprotein cofactor that is needed for enzymic activity. Commonly encountered cofactors include metal ions such as Zn2+ or Fe2+, and organic molecules, known as coenzymes, that are often derivatives of vitamins. For example, the coenzyme NAD+contains niacin, FAD contains riboflavin, and coenzyme A contains pantothenic acid. (See pp. 371-379 for the role of vitamins as precursors of coenzymes.) Holoenzyme refers to the enzyme with its cofactor. Apoenzyme refers to the protein portion of the holoenzyme. In the absence of the appropriate cofactor, the apoenzyme typically does not show biologic activity. A prosthetic group is a tightly bound coenzyme that does not dissociate from the enzyme (for example, the biotin bound to carboxylases, see p. 379). 

Pantothenic acid is a vitamin, which is essential to human life. Its name is derived from a Greek root that reflects its universal occurrence in living things. The bacterium Lactobacillus bulgaricus, which converts milk... 

Fig. 1. Structure of CoA, composed of three parts a nucleotide pan derived from 3 -adenosine-5 -pbosphate, forming a phosphodiester bond with a 4-phospho derivative of pantothenic acid, and a third pan derived horn the amino acid, cysteine. The side chain SH group of the latter is ftee in this compound and is readily acylated, and thus able to act as a carrier for acyl groups in biochemical reactions in which it transfers that group between two substrates...

LM Lewin, R Golan, O Wassercug, S Green. Bioautographic identification of coenzyme A, pantothenic acid and derivatives. J Micronutr Anal 4 209-216,1988. 

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