604801-31-2Relevant academic research and scientific papers
Synthesis of 3′-acetamidoadenosine derivatives as potential A 3 adenosine receptor agonists
Chun, Moon Woo,Choi, Sung Wook,Kang, Tae Kyung,Choi, Won Jun,Kim, Hea Ok,Gao, Zhan-Guo,Jacobson, Kenneth A.,Jeong, Lak Shin
, p. 408 - 420 (2008/09/19)
On the basis of high binding affinity of 3′-aminoadenosine derivatives 2b at the human A3 adenosine receptor (AR), 3′- acetamidoadenosine derivatives 3a-e were synthesized from 1,2:5,6-di-O- isopropylidene-D-glucose via stereoselective hydroboration as a key step. Although all synthesized compounds were totally devoid of binding affinity at the human A3AR, our results revealed that 3′-position of adenosine can only be tolerated with small size of a hydrogen bonding donor like hydroxyl or amino group in the binding site of human A3AR. Copyright Taylor & Francis Group, LLC.
3′-C-branched-chain-substituted nucleosides and nucleotides as potent inhibitors of Mycobacterium tuberculosis thymidine monophosphate kinase
Vanheusden, Veerle,Munier-Lehmann, Hélène,Froeyen, Matheus,Dugué, Laurence,Heyerick, Arne,De Keukeleire, Denis,Pochet, Sylvie,Busson, Roger,Herdewijn, Piet,Van Calenbergh, Serge
, p. 3811 - 3821 (2007/10/03)
Thymidine monophosphate kinase (TMPK) of Mycobacterium tuberculosis (TMPKmt) represents an attractive target for blocking the bacterial DNA synthesis. In an attempt to find high-affinity inhibitors of TMPKmt, a cavity in the enzyme at the 3′-position was
Nucleosides and nucleotides. 147. Synthesis of DNA dodecamers containing oxetanocin A and (2R, 3R)-2-C-(adenin-9-yl)-1,4-anhydro-2,3-dideoxy-3-C-hydroxymethyl-D-arabitol
Kakefuda, Akio,Masuda, Akira,Ueno, Yoshihito,Ono, Akira,Matsuda, Akira
, p. 2863 - 2876 (2007/10/03)
Oxetanocin A (1) and (2R,3R)-2-C-(adenin-9-yl)-1,4-anhydro-2,3-dideoxy-3-C-hydroxy-methyl-D-arabitol (2), a ring-expanded oxetanocin analogue, were incorporated into DNA dodecamers, 5′-d(CGCG1ATTCGCG)-3′ (II), 5′-d(CGCGA1TTCGCG)-3′ (III), 5′-d(CGCG2ATTCGCG)-3′ (IV), and 5′-d(CGCGA2TTCGCG)-3′ (V). Thermally induced transitions of II, III, IV, and V together with a parent dodecamer, 5-d(CGCGAATTCGCG)-3′ (I) were monitored at 260 nm in a buffer containing 0.01 M sodium phosphate (pH 7.0), 0.02 M NaCl, and 6 μM of each dodecamer. The order of Tms was 40 °C (I) > 37 °C (IV) > 36 °C (V) > 34 °C (II) > 32 °C (III). The oligonucleotide containing 2 was more resistant to snake venom phosphodiesterase than unmodified DNA dodecamer (I).
