N^G-Hydroxyguanidines from Primary Amines

Abstract

A concise and general method for the preparation of N(G)-hydroxyguanidines from primary amines is reported. Using available and readily prepared materials, primary amines are converted to protected N(G)-hydroxyguanidines in a one-pot procedure followed by deprotection under nonreducing conditions. The method has been successfully applied to a number of examples including a high-yielding preparation of N(G)-hydroxy-L-arginine, the intermediate in the enzymatic conversion of L-arginine to nitric oxide and L-citrulline by nitric oxide synthase.

Protein Arginine N‐Methyltransferase Substrate Preferences for Different Nη‐Substituted Arginyl Peptides

“…The Nh-modified hydroxy-larginine and amino-l-arginine building blocks were prepared by previously described approaches. [32][33][34] Fmoc-l-nitroarginine was obtained from Bachem (Bubendorf, Switzerland). l-Canavanine was obtained from Sigma-Aldrich and converted into the Boc/Fmocprotected species required for Fmoc SPPS based upon a previously reported protocol.…”

Reactivity of cyclic alkoxyguanidines – experimental and theoretical studies

“…3 Thus far, however, the chemical properties of alkoxyguanidine functionality have been poorly investigated and are limited to the scission of the N-O bond. 4,5 Thus, the next logical step in the development of this chemistry was to study the reactivity of highly soluble cyclic alkoxyguanidines (B) in other solvents (Scheme 1). …”

Novel guanidinyl pyrrolidine salt-based bifunctional organocatalysts: application in asymmetric conjugate addition of malonates to enones

“…Compounds Ia, Ib and Ic were efficiently synthesised in three steps according to slightly modified literature procedure starting from (S)-N-Boc-aminomethylpyrrolidine (see ESI for Supplementary data). 19 The investigation was started by evaluating the catalysts ability to promote conjugate addition of malonates to cyclohexenone 1 under neat conditions at room temperature. As shown in Table 1 the use of 10 mol % of free base catalysts Ia, Ib and Ic and dimethylmalonate as the nucleophile led to a total conversion but afforded a racemic product.…”