Adenylic acid monophosphates

Adenine Adenosine Adenylic acid Adenosine monophosphate (AMP) Adenosine diphosphate (ADP) Adenosine triphosphate (ATP)... 

ADENOSINE PHOSPHATES. The adenosine phosphates include adenylic acid (adenosine monophosphate, AMP) in which adenosine is esteri-fied with phosphoric add at the 5/-position adenosine diphosphate (ADP) in which esterification at the same position is with pyrophosphoric acid,... 

Rival 1c acid, AE74 Plvalophenone, ATTO Poly(adenylIc acid), AR82 Poly(cytidy) ic acid), APT6 Poly(uridin e-31-monophosphate), AP56... 

Adenosine 5 -phosphate is also known as AMP (for adenosine monophosphate) or adenylic acid. If deoxyribose replaces ribose in adenosine 5 -phosphate, the terminology is dAMP or deoxyadenylic acid. The abbreviated names for some ribonucleotides and deoxyribonucleotides are listed below. 

CAS 61-19-8. C10H14N5O7P. The monophosphoric ester of adenosine, i.e., the nucleotide containing adenine, d-ribose, and phosphoric acid. Adenylic acid is a constituent of many important coenzymes. Cyclic adenosine-3, 5 -monophosphate is designated by biochemists as cAMP. 

Adenine (6-aminopurine) Adenosine Deoxyadenosine Adenosine monophosphate (AMP) or adenylic acid Deoxyadenosine monophosphate (dAMP)... 

Nucleotides are phosphoric acid esters of nucleosides. The 5 -monophosphate of adenosine is called 5 -adenylic acid or adenosine 5 -monophosphate (AMP). 

Eibonucleoside 5 -phosphates possess an unsubstituted, vicinal cis-glycol system. Such systems complex with boric acid, and an increase in the acidity results. In addition, these a-m-glycol systems are cleaved by metaperiodate to their corresponding dialdehydes. Thus, adenosine 5 -phosphate consumes one mole of periodate per mole, whereas yeast adenylic acid (the 2 - and 3 -monophosphates of adenosine see p. 312) is resistant to this oxidant. ... 

Adenylic Acid. Adenosine 3 -monophosphate adenosine - 3 -phosphoric acid adenosine - 3 -monophos-phoric acid adenylic acid b yeast adenylic acid synadenylic acid h-adenylic acid. C HuNjOyP mol wt 347.23. C 34.59%, H 4.06%, N 20.17%, O 32.26%, P 8.92%. Early prepns from yeast nucleic acid Levene. Bass, Nucleic Acids, (Chemical Catalogue Co., New York, 1931). Early work probebty done on mixtures of 2 - and 3 -adenylic acids both compds isomerize readily to form an equilibrium mix -Hire under acid conditions Carter, Cohn, Fed. Proc. 8, 190 (1949) Baddily, in The Nucleic Acids vol. 1, E. Chargaff, J. N. Davidson, Eds. (Academic Press, New Yotk, 1955) pp 165-168 A. M. Michelson, The Chemistry of Nucleoside and Nucleotides (Academic Press, New York, 1963) pp 100-106. Synthesis Brnwn, Todd, J. Chem. Soc. 1952, 44. Structure nf dihydrate Brown el at, Nature 172, 1184... 

Adenylic Acid. Muscle adenylic acid ergaden -ylic acid t -adenylic acid adenosine S -monophosphate adenosine phosphate adenosine-5 -phosphoric add edeno-sine-5. monophosphoric acid A5MP AMP NSC-20264 Addiyl Cardiomone (Na salt) Lycedan My -B-Den My-oston Phosaden. C,0HhNjO7P mol wt 347.23, C 34.59%, H 4.06%, N 20.17%, O 32,25%, P 8,92%. Nucleotide widely distributed in nature. Prepn from tissues Embden, Zimmerman, Z. Physrot Chem. 167, 137 (1927) Embden, Schmidt, ibid. 181, 130 (1929) cf. Kalckar, J. B.ol Chem. 167, 445 (1947). Prepn by hydrolysis of ATP with barium hydroxide Kerr, 3. Biot Chem. 139, 13l (1941). Synthesis Baddiley, Todd. 3. Chem. Soc. 1947, 648. Commercial prepn by enzymatic phosphorylation of adenosine. Monograph on synthesis of nucleotides G. R. Pettit. Synthetic Nucleotides vol, 1 (Van Nostrand-Reinhold. New York, 1972) 252 pp. Crystal structure Kraut, lensen, Acta Cryst 16, 79 (1963). Reviews see Adenosine Nucleic Acids. 

Abbreviations used NAD+ = nicotinamide adenine dinucleotide NADH e reduced nicotinamide adenine dinucleotide NADP = nicotinamide adenine dinudeotide phosphate NAD PH reduced nicotinamide adenine dinucleotide phosphate NMN, NMN+ nicotinamide mononucleotide NMNH2 = reduced nicotinamide mononucleotide a-NAD a-nicotinamide adenine dinucleotide AMP = 5 -adenylic acid 3,5 -AMP adenosine 3, 5 -cycIic phosphate 3 ,5 -UMP = uridine 3, 5 -cyclic phosphate 3, 5 -CMP cytidine 3, 5-cyclic phosphate 3 f5 GMP = guanosine 3 5f-cyclic phosphate 3, 5 TMP thymidine 3, 5 -cyclic phosphate Dibutyryl-3, 5 -AMP = N6,02-dibutyryladenosine 3, 5 -cyclic phosphate 2, 3 -UMP = uridine 2 ,3 -cyclic monophosphate 2, 3 -CMP cytidine 2, 3 -cyclic monophosphate 2, 3 -AMP = adenosine 2, 3 -cyclic monophosphate 2 ,3 -GMP = guanosine 2 3 -cyclic monophosphate 2 -UMP = uridine 2 -phosphate -UMP uridine -phosphate 5 -UMP = uridine 5 phosphate Poly U polyuridylic acid ADP = adenosine 5 -diphosphate FAD = flavin adenine dinucleotide UpA, UpU, ApU and ApA x dinucleoside phosphates of uridine and/or adenine. c See original references for experimental conditions and additional data. 

Adenosine phosphate CAS 61-19-8 EINECS/ELINCS 200-500-0 Synonyms Adenosine monophosphate Adenosine-5 -monophosphate Adenosine-5 -monophosphoric acid 5 -Adenylic acid AMP Ciassification Heterocyclic org. compd. 

Nucleotides are named in several ways. Adenylic acid (Fig. 25.3), for example, is usually called AMP, for adenosine monophosphate. The position of the phosphate group is sometimes explicitly noted by use of the names adenosine 5 -monophosphate or 5 -adenylic acid. Uridylic acid is usually called UMP, for uridine monophosphate, although it can also be called uridine 5 -monophosphate or 5 -uridylic acid. If a nucleotide is present as a diphosphate or triphosphate, the names are adjusted accordingly, such as ADP for adenosine diphosphate or GTP for guanosine triphosphate. 

The different varieties of orthophosphoric monoesters and diesters which are present in all living species are exceedingly numerous. Biologically important monoesters include the mononucleotides such as, for example, adenylic acid (adenosine monophosphate, AMP), inosinic acid, vitamin Bg and many phosphorylated proteins, for example, milk caseins. Biologically important diesters include the phospholipids (e.g. lecithin and phosphatidyl inositol), plasmalogens, sphingomyelins, cyclic nucleotide monophosphates (e.g. cyclic AMP), some teichoic acids, vitamin Bj2 and of course the immensely important nucleic acids (polynucleotides) (Chapters 10 and 11). The great stability of diesters is an essential feature of the chemistry of polynucleotides. 

The RNA mononucleotide unit containing adenine is adenosine-5 -monophosphate (adenylic acid) (AMP). This compound is described in Chapter 11.3 and is the hydrolysis product from adenosine triphosphate (ATP). 

Adenosine 5 -phosphate. Adenosine 5 -monophosphate. Adenosine-5 -phosphoric acid. Muscle adenylic acid. AMP. 5 -Adenylic acid. Phosphaden. NSC 20264 [61-19-8]... 

Describe a nucleotide. Draw the structural formula for deoxycytidine monophosphate, analogous to deoxy-adenylic acid, in which cytosine is the organic base. 

The separation of nucleotides and deoxynucleotides, previously a formidable task involving the fractional crystallization of heavy metal and alkaloid salts 102) has been made much easier by developments in analytical techniques. Ion-exchange methods may be used for the purification, isolation, and identification of both classes of nucleotides from hydrolysis mixtures 103), Countercurrent distribution 104) and starch 106) and cellulose-column 106) as well as paper-strip chromatography 107) have also proved to be useful in separating nucleotides from natural sources. Spectro-photometric procedures based on the characteristic ultraviolet absorption spectra of the purines and pyrimidines have been the most convenient method to locate, estimate, and identify the fractions obtained in the previous separations. Since the nucleotides are acid in nature, they are often named as acids, e.g., adenylic acid, cytidylic acid. The general constitution of the purine nucleotides (and by analogy the pyrimidine nucleotides) is demonstrated by their hydrolysis by acids to a purine and ribose (or 2-deoxyribose) monophosphate and by alkalies to the nucleosides and phosphoric acid. The order of the constituents in a purine nucleotide must, therefore, be ... 

Adenosine triphosphate (ATP) was isolated from muscle by Lohmann in 1928. The three terminal phosphate groups of ATP are joined by two anhydride bonds. Removal of the terminal phosphate gives adenosine diphosphate (ADP), and of the next phosphate leaves adenosine monophosphate (AMP) or adenylic acid. 

The purine base adenine (6-aminopurine, previoulsy also known as vitamin B4,5-131) is generally widespread as a building unit of the ribofuranoside adenosine and its phosphates, such as adenosine 5 -monophosphate (AMP, adenylic acid), adenosine 5 -diphosphate (ADP) and adenosine 5 -triphosphate (ATP), polynucleotides, such as ribonucleic acid (RNA) and deoxyribonucleic acid (DNA), vitamins (riboflavin, adenosylvitaminBjj) and cofactors NAD(P)+ and FAD. Adenylic acid was once considered a member of the vitamin B complex (as vitamin Bg). The agent in shiitake (Lenttnula edodes) mushrooms that can reduce the level of cholesterol in the blood is a purine derivative, (2fi,3fi)-dihydroxy-4-(9-adenyl)butyric acid (5-132) called eritadenine (lentinacin, lentysine). 

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