Liquid and solid phase syntheses of orthogonally protected α-hydrazinoacid derivatives

Syntheses of Hydrazino Peptides and Conjugates

“…[1] Further replacement of the C-α and/or C-β atom of the β-amino acid constituent by a hetero atom is another attractive extension of the β-peptide concept. [3] The vitamin B6 antagonist linatine (1) and the antibiotic negamycin (2) are naturally occurring peptides that contain such a α-hydrazino acid moiety (see Figure 1). [3] The vitamin B6 antagonist linatine (1) and the antibiotic negamycin (2) are naturally occurring peptides that contain such a α-hydrazino acid moiety (see Figure 1).…”

Solution‐phase submonomer diversification of aza‐dipeptide building blocks and their application in aza‐peptide and aza‐DKP synthesis

“…As mentioned earlier, phthalimide protection has been used for the synthesis of N ‐alkyl, N ‐acyl hydrazines in solution‐ and on solid‐phase30, 32–35. Mitsunobu alkylation of N ‐acylaminophthalimides provided good yields of alkylated products using primary, secondary and benzyl alcohols30.…”

Synthesis and Chemistry of α‐Hydrazino Acids

“…Treatment of 6 with methylhydrazine allowed the smooth deprotection of the phthalimide moiety yielding N 1 -protected a-hydrazino esters 7 in fair to very good overall yield, excellent enantiomeric excess, and with inverted configuration [100]. Solid-phase synthesis of orthogonally N 1 ,N 2diprotected a-hydrazino esters was also developed using this strategy [102]. Solid-phase synthesis of orthogonally N 1 ,N 2diprotected a-hydrazino esters was also developed using this strategy [102].…”