Nα-Z-Nε-Azido-L-Lysine cyclohexylammonium salt

A simple and efficient method for the preparation of α-D-ribose 1-phosphate and 2-deoxy-α-D-ribose 1-phosphate, key intermediates in nucleoside metabolism and important starting compounds for the enzymatic synthesis of various modified nucleosides, has been proposed. It consists in near-irreversible enzymatic phosphorolysis of readily prepared hydroiodide salts of 7-methylguanosine and 7-methyl-2'-deoxyguanosine, respectively, in the presence of purine nucleoside phosphorylase. α-D-Ribose 1-phosphate and 2-deoxy-α-D-ribose 1-phosphate are obtained in near quantitative yields (by HPLC analysis) and 74%-94% yields after their isolation and purification. © 2022 Wiley Periodicals LLC. Basic Protocol 1: Preparation of α-D-ribose 1-phosphate barium salt (4a) Alternate Protocol 1: Preparation of 2-deoxy-α-D-ribose 1-phosphate barium salt (4b) Basic Protocol 2: Preparation of α-D-ribose 1-phosphate bis(cyclohexylammonium) salt (5a) Alternate Protocol 2: Preparation of 2-deoxy-α-D-ribose 1-phosphate bis(cyclohexylammonium) salt (5b).

In the title molecular salt, 2C(6)H(14)N(+)·C(14)H(8)O(4)S(2) (2-), the complete dianion is generated by crystallographic twofold symmetry and a twisted conformation is found [the C-S-S-C torsion angle is 87.13 (2)° and the dihedral angle between the rings is 83.4 (2)°]. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the cations and anions.

In the title salt, C6H14N(+)·NO3 (-), the cyclo-hexyl ring adopts a chair conformation. The ammonium group occupies an equatorial position and the crystal struture is stabilized by inter-molecular N-H⋯O hydrogen-bonding inter-actions, resulting in a three-dimensional network.