Synthesis of polysarcosine from air and moisture stable N-phenoxycarbonyl-N-methylglycine assisted by tertiary amine base

Abstract

Polysarcosine (Mn = 3650-20 000 g mol-1, D [similar] 1.1) was synthesized from the air and moisture stable N-phenoxycarbonyl-N-methylglycine. Polymerization was achieved by in situ transformation of the urethane precursor into the corresponding N-methylglycine-N-carboxyanhydride, when in the presence of a non-nucleophilic tertiary amine base and a primary amine initiator

Convenient synthetic approach to poly(N‐Methyl L‐alanine) through polycondensation of activated urethane derivative of N‐methyl L‐alanine

“…Polypeptoids ( N ‐substituted glycines) are known to be one of the polypeptide mimics, in which the substituent position is shifted from the α‐carbon to the amide nitrogen . Recently, these polypeptoids has much attentions such as (1) enhanced solubility, compared with both natural and synthetic polypeptide because of the lack of hydrogen bonding, (2) biodegradability by oxidative degration .…”

Thermoresponsive polysarcosine-based nanoparticles

“…4 Consequently, PSar offers a real alternative to poly(ethylene glycol) (PEG) for numerous applications, 5 including its use as a non-fouling coating, 6 and therapeutic protein conjugation. 7 The precise control over PSar synthesis has enabled the accurate synthesis of block copolymers that contain PSar conjugated to other polypeptoids, [8][9][10] poly(ε-caprolactone), 11,12 tertiary aminecontaining molecules, 13 PEG, 14 and poly(amino acids)/polyamides. [15][16][17] There has been much recent interest in the application of PSar for the controlled release of therapeutic compounds.…”

Well‐defined, environment‐friendly synthesis of polypeptides based on phosgene‐free transformation of amino acids into urethane derivatives and their applications

“…By contrast to poly( l ‐alanine), which is insoluble in any solvent, poly( N ‐methyl‐ l ‐alanine) is soluble in a wide range of solvents including water. Similarly, by polymerization of the N ‐methyl urethane derivative of glycine, a well‐defined poly( N ‐methyl glycine), known as poly(sarcosine), can be synthesized precisely . Poly( N ‐methyl glycine) is water soluble and biocompatible, and its application in medical materials is expected.…”