Pantothenic acid structure

Figure 1 shows the structure of pantothenic acid ((R)-(+)-N-(2,4-dihydroxy-3,3 -dimethyl-1 -oxobuty 1-13-alanine). Only D(+)-pantothenic acid occurs naturally and is biologically active. The alcohol (R)-pantothenol (= (D)-panthenol) shows biological activity as well. 

Pantothenic Acid. Figure 1 Structure of pantothenic acid. 

FIGURE 10.8 Structural formula of P-alanine and pantothenic acid. 1 — P-[3- H]alanine, 2 — D-[3- H]pantothenic acid, 3 — D-[l- C]panthothenic acid. Boldfaced letter H or C denotes radioactivity. 

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... 

Pantothenic acid is a component of coenzyme A, which functions in the transfer of acyl groups (Figure 28.17). Coenzyme A contains a thiol group that carries acyl compounds as activated thiol esters. Examples of such structures are succinyl CoA, fatty acyl CoA, and acetyl CoA. Pantothenic acid is also a component of fatty acid synthase (see p. 182). Eggs, liver, and yeast are the most important sources of pan tothenic acid, although the vitamin is widely distributed. Pantothenic acid deficiency is not well characterized in humans, and no RDA has been established. 

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...

In 1940, Hams, Folkers, ct al. reported structure determination and synthesis and crystallization of pantothenic acid. In 1950. Lipmaiin el al. discovered coenzyme A and, in 1951, Lynen characterized the coenzyme A structure,... 

Phosphopantetheine coenzymes are the biochemically active forms of the vitamin pantothenic acid. In figure 10.11, 4 -phosphopantetheine is shown as covalently linked to an adenylyl group in coenzyme A or it can also be linked to a protein such as a serine hydroxyl group in acyl carrier protein (ACP). It is also found bonded to proteins that catalyze the activation and polymerization of amino acids to polypeptide antibiotics. Coenzyme A was discovered, purified, and structurally characterized by Fritz Lipmann and colleagues in work for which Lipmann was awarded the Nobel Prize in 1953. 

Structures of the vitamin pantothenic acid (in red) and coenzyme A. The terminal —SH (in blue) is the reactive group in coenzyme A (CoASH). 

The uptake and accumulation of various amino acids in Lactobacillus arabinosus have been described. Deficiencies of vitamin B6, biotin, and pantothenic acid markedly alter the operation of these transport systems. Accumulation capacity is decreased most severely by a vitamin B6 deficiency. This effect appears to arise indirectly from the synthesis of abnormal cell wall which renders the transport systems unusually sensitive to osmotic factors. Kinetic and osmotic experiments also exclude biotin and pantothenate from direct catalytic involvement in the transport process. Like vitamin B6, they affect uptake indirectly, probably through the metabolism of a structural cell component. The evidence presented supports a concept of pool formation in which free amino acids accumulate in the cell through the intervention of membrane-localized transport catalysts. 

Coenzyme A is an adenine nucleotide at one end, linked by a S -pyrophosphate to pantothenic acid, a compound that looks rather like a tripeptide, and then to an amino thiol. Here is the structure broken down into its parts. 

Figure 9-22 Structural Formula of Pantothenic Acid. Pantothenic acid R = COOH Panthenol R = CH2OH.

Coenzyme A (abbreviated CoA or CoASH, 6) was discovered by Lipmann in the 1940s, and its structure was first reported in 1953 (2, 3). The structure of CoA consists of 3 -phosphoadenosine and pantetheine, linked by a pyrophosphate group (Fig. 1). The pantetheine moiety is derived from pantothenic acid 1, also known as vitamin B5. CoA and its... 

FIGURE 431 Coen -yfne A- The vitamin, pantothenic acid, occurs as part of the structure of coenzyme A,... 

Although the water-soluble vitamins are structurally diverse, they are put in a general class to distinguish them from the lipid-soluble vitamins. This cla.ss includes the B-complex vitamins and ascorbic acid (vitamin C). The term B-complex vitamins usually refers to thiamine, riboflavin, pyridoxine. nicotinic acid, pantothenic acid, hiotin. cyanocobalamin. and folic acid. Dietary deficiencies of any of the B vitamins commonly are complicated by deftciencies of another mem-ber(s) of the group,. so treatment with B-complex preparations is usually indicated. 

The metabolic functions of pantothenic acid in human biochemistry are mediated through the synthesis of CoA. Pantothenic acid is a structural component of CoA. which is necessary for many important metabolic processes. Pantothenic acid is incorporated into CoA by a. series of five enzyme-catalyzed reactions. CoA is involved in the activation of fatty acids before oxidation, which requires ATP to form the respective fatty ocyl-CoA derivatives. Pantothenic acid aI.so participates in fatty acid oxidation in the final step, forming acetyl-CoA. Acetyl-CoA is also formed from pyruvate decarboxylation, in which CoA participates with thiamine pyrophosphate and lipoic acid, two other important coenzymes. Thiamine pyrophosphate is the actual decarboxylating coenzyme that functions with lipoic acid to form acetyidihydrolipoic acid from pyruvate decarboxylation. CoA then accepts the acetyl group from acetyidihydrolipoic acid to form acetyl-CoA. Acetyl-CoA is an acetyl donor in many processes and is the precursor in important biosyntheses (e.g.. those of fatty acids, steroids, porphyrins, and acetylcholine). 

Most vitamins function either as a hormone/ chemical messenger (cholecalciferol), structural component in some metabolic process (pantothenic acid), or a coenzyme (phytonadi-one, thiamine, riboflavin, niacin, pyridoxine, biotin, folic acid, cyanocobalamin). At least one vitamin has more than one biochemical role. Vitamin A as an aldehyde (retinal) is a structural component of the visual pigment rhodopsin and, in its acid form (retinoic acid), is a regulator of cell differentiation. The precise biochemical functions of ascorbic acid and a-tocopherol still are not well defined. 

Pantothenic acid is a structural component, but not the active site, of coenzyme A The acyl thiol esters form on the mercaptan moiety that originates from a cysteine (Fig. 8.39). The biosynthesis of coenzyme A occurs in the tissues requiring it. Because coenzyme A is required for nearly all acyl transfers, biosynthesis takes place in nearly all cells. 

Pantothenic acid is a precursor for the synthesis of coenzyme A (CoA, CoASH) and forms part of the swinging sulfhydryl arm of the fatty acid synthase complex (Chapter 19). Its structure is shown in Figure 38-20. 

The structure and function of pantothenic acid are discussed in Appendix F, Water-Soluble Vitamins. 

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