5'-chloro-5'-Deoxyadenosine (hydrate) is a nucleoside analog used as a substrate in polyketide biosynthesis. S-(5'-adenosyl)-L-methionine can be converted to 5'-chloro-5'-deoxyadenosine in a reaction catalyzed by a SAM-dependent chlorinase. Through a 7-step route, 5'-chloro-5'-deoxyadenosine can be converted to chloroethylmalonyl-CoA, which has been shown to be involved in the biosynthesis of the anticancer agent salinosporamide A in the marine bacterium S. tropica.
2'-Deoxyadenosine-5'-triphosphate (dATP) is a purine nucleotide and derivative of the nucleic acid adenosine 5'-triphosphate .1dATP is a substrate for DNA polymerase in the synthesis of DNA.2It is a noncompetitive inhibitor of ribonucleotide reductases, which provides feedback inhibition during DNA synthesis.1dATP has commonly been used in DNA synthesis, sequencing, and labeling in research applications.3,4dATP accumulates in adenosine deaminase deficiency, a disorder characterized by mutations in the gene for adenosine deaminase, the enzyme that catalyzes the deamination of adenosine and deoxyadenosine.5 1.Berg, J.M., Tymoczko, J.L., and Stryer, L.Key steps in nucleotide biosynthesis are regulated by feedback inhibitionBiochemistry(2002) 2.Berg, J.M., Tymoczko, J.L., and Stryer, L.DNA is replicated by polymerases that take instructions from templatesBiochemistry(2002) 3.Cadwell, R.C., and Joyce, G.F.Randomization of genes by PCR mutagenesisPCR Methods Appl.2(1)28-33(1992) 4.Steffens, D.L., Jang, G.Y., Sutter, S.L., et al.An infrared fluorescent dATP for labeling DNAGenome Res.5(4)393-399(1995) 5.Flinn, A.M., and Gennery, A.R.Adenosine deaminase deficiency: A reviewOrphanet J. Rare Dis.13(1)65(2018)
SAHO is a sulfoxide form of the methyl donor S-(5'-adenosyl)-L-methionine chloride and a substrate for radical SAM enzymes.1It is reductively cleaved to S-adenosylhomocysteine , 5'-deoxyadenosine , and 5'-thioadenosine sulfenic acid by the radical SAM enzymes NosL or NosN. 1.Mandalapu, D., Ji, X., and Zhang, Q.Reductive cleavage of sulfoxide and sulfone by two radical S-adenosyl-L-methionine enzymesBiochemistry58(1)36-39(2019)
SAHO2is a sulfone form of the methyl donor S-(5'-adenosyl)-L-methionine chloride and is a substrate for radical SAM enzymes.1It is reductively cleaved to 5'-deoxyadenosine and 5'-thioadenosine sulfinic acid by the radical SAM enzymes NosL or NosN. 1.Mandalapu, D., Ji, X., and Zhang, Q.Reductive cleavage of sulfoxide and sulfone by two radical S-adenosyl-L-methionine enzymesBiochemistry58(1)36-39(2019)
2'-NH2-ATP (2'-Amino-2'-deoxyadenosine-5'-triphosphate) is an adenosine derivative compound that acts as a weak competitive inhibitor of ATP with a K i value of 2.3 mM. It finds utility in nucleic acid labeling.