A Sequential C-N, C-C Bond-Forming Reaction: Direct Synthesis of α-Amino Acids from Terminal Alkynes

Lee, Alison V.; Schafer, Laurel L.

doi:10.1055/s-2006-944211

Cited by 6 publications

(2 citation statements)

References 6 publications

(8 reference statements)

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“…Schafer et al also reported the synthesis of this material from its amide precursor via acid hydrolysis. 37 However, they have reported yield of <30%. Using alkaline hydrolysis pure amino acid with a reasonable yield (40%) was isolated using this synthesis method.…”

Section: Resultsmentioning

confidence: 98%

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Synthesis of Polypeptides and Poly(α-hydroxy esters) from Aldehydes Using Strecker Synthesis

Abtew,

Domb

2023

ACS Omega

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This report presents a versatile approach for the synthesis of new polypeptide and polyester-based biomaterials. The well-established Strecker reaction was utilized, with hexanal serving as the model aldehyde, to synthesize α-amino and α-hydroxy acids as monomer units for the polymer system. Following the formation of the corresponding amino and hydroxy acid monomers, they were subsequently converted to N-carboxy and O-carboxy-anhydrides. The resultant cyclic anhydride molecules were then polymerized via ring-opening polymerization to yield the corresponding polypeptides and polyesters. This report establishes a straightforward methodology for the synthesis of new polypeptide and poly(a-hydroxy acid)-based biomaterials, thereby expanding the existing library of polymers for various biomedical applications.

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Section: Resultsmentioning

confidence: 98%

“…The amide obtained in the previous step was further hydrolyzed to a carboxylic acid in an aqueous alkaline solution. Schafer et al also reported the synthesis of this material from its amide precursor via acid hydrolysis . However, they have reported yield of <30%.…”

Section: Resultsmentioning

confidence: 99%