The Effect of Replacement of the Carboxamide Group by Hydrogen in the Glutamine or Asparagine Residue of Oxytocin on Its Biological Activity

Synthesis and some of the pharmacological properties of [4-leucine]-8-lysine-vasopressin and [1-deamino,4-leucine]-8-lysine-vasopressin

“…Indeed, the formal replacement of this group by a hydrogen atom to give [4-decarboxamido]oxytocin ([4-a-aminobutyric acid]oxytocin) yielded an analog which possesses high oxytocic and avian vasodepressor (AVD) activities. 3 All of the compounds in this series of analogs have extremely low or negligible antidiuretic (ADH) and rat pressor activities. In fact, [4-leucine] oxytocin was actually found to possess the opposite effects (i.e., diuretic and depressor effects) in the rat.…”

“…AChE. Additional analogs were desired to evaluate the requirement for a rigid 180°torsional angle imposed on the N-Cq-C(3-C7 and Ca-Cg-C7-Cg chains in 1 and 2, those portions of the inhibitor simulating the analogous N-Ca-C#?-O and CorC/3-O-C fragments in ACh (3). Furthermore, the ether oxygen and the 2-methyl group were questionable requirements for binding of 1 and 2 to AChE.…”

Structure of the Cell Wall of Staphylococcus aureus. VIII. Structure and Chemical Synthesis of the Basic Peptides Released by the Myxobacterium Enzyme*

“…The following compounds were prepared as previously described: carbobenzoxy-L-alanine (Bergmann and Zervas, 1932), carbobenzoxy-D-alanine (Hunt and du Vigneaud, 1938), e-carbobenzoxy-L-lysine (Bergmann et al, 1935), carbobenzoxyglycine pnitrophenyl ester (du Vigneaud et al, 1960), carbobenzoxy-L-alanine p-nitrophenyl ester (du Vigneaud et al, 1964), and a-o-nitrophenylsulfenyl-(e-carbobenzoxy)-L-lysine dicyclohexylammonium salt (Zervas et al, 1963). These compounds gave satisfactory analytical values and their melting points and optical rotations were in agreement with the published values.…”