Amino analogue

Yang JS, Huang GJ, Liu YH, Peng SM (2008) Photoisomerization of the green fluorescence protein chromophore and the meta- and para-amino analogues. Chem Commun 1344-1346... 

Another application of diastereoselective nitro-aldol reactions catalyzed by Bu4NF-3H20 is demonstrated in a simple synthesis of l,4-dideoxy-l,4-imino-D-mannitol (DIM) and amino analogues (Eq. 3.85).134 The nitro-aldol reaction of nitro compounds bearing a-oxy or a-amino function with glyceraldehyde leads to nitrohexitols, which can be reduced to the corresponding amino compounds. Cyclization gives iminopolyols, as shown in Eq. 3.85. 

K., Wachter, H., Werner-Felmayer, G., Mayer, B., Identification of the 4-amino analogue of tetrahydrobiopterin as a dihydropteridine reductase inhibitor and a potent pteridine antagonist of rat neuronal nitric oxide synthase, Biochem. J. 320 (1996), p. 193-196... 

Traces (0.1%) of 2-l luoro-/)-alanine were also found in the urine of patients treated with the antifungal agent flucytosine (5-fluorocytosine, 4.239) [156], However, it appears that flucytosine, the amino analogue of 5-fluoro-... 

Knight, W.B. and Cleland, W.W., Thiol and amino analogues as alternate substrates for glyc-erokinase from Candida mycoderma, Biochemistry, 28, 5728,1989. 

UV Absorptions of (32 R = H) in ether (Table 5) <85ZAAC(525)ll2> bear little resemblance to UV spectra of amino analogues (32 R = NHj, NMej, NHC02Et) either in acid or in basic solutions. Absorption bands for the dithiazole cation (31 R = R = NMcj) <87BCJ2686> are markedly shifted relative to bands of the unsubstituted diamino cation in ethanol (31 R = R = NH2) <84CHEC-I(6)897>. UV spectral comparison of (34 X = O, R = N=CHPh, R = Ph) with the other two derivatives (34 X = O) in Table 5 was used in structural assignment <91JHC1957>. 

Reduction of the 4-azido moiety of the 5-[4-azido]oxadiazolyltriazolooxadiazole 36 with stannous chloride yielded the amino analogue 133 (Scheme 18) <1993HCA1>. 

F. W. Lichtenthaler and S. Mondel, Manno- and altro-sucrose, and some amino-analogues,... 

Aminopterin and amethopterin are 4-amino analogues of folic acid (Fig. 11.5) and as such are potent inhibitors of the enzyme dihydrofolate reductase (EC 1.5.1.3) (Blakley, 1969). This enzyme catalyses the reduction of folic acid and dihydrofolic acid to tetrahy-drofolic acid which is the level of reduction of the active coenzyme involved in many different aspects of single carbon transfer. As is clear from Fig. 11.6, tetrahydrofolate is involved in the metabolism of (a) the amino acids glycine and methionine (b) the carbon atoms at positions 2 and 8 of the purine ring (c) the methyl group of thymidine and (d) indirectly in the synthesis of choline and histidine. 

Aminopterin and amethopterin (methotrexate) are 4-amino analogues of folic acid (Fig. 11.3) and interfere with the production of the active folate coenzyme by blocking the enzyme dihydrofolate reductase (reaction b in Fig. 13.1) (see also Fig. 11.6). 

Treatment of compound (10b) with stannous chloride effected reduction giving the amino analogue (lOd) (Scheme 9) <93HAC52l>. 

This section deals with the comparatively new anhydro-4-hydroxyoxazolium hydroxides (217), the isomeric 5-hydroxy compounds (218) and the amino analogues (219). The chemistry of the munchnones (218) has been intensively studied as a result of the pioneering research of Huisgen s school in Munich on 1,3-dipolar cycloaddition reactions of these compounds (B-67MI41800). There have been so many publications in this area that only the bare outlines can be presented here the reader is referred to recent reviews (76AHC(19)1, 81MI41800) for fuller accounts. 

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