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Title: Submonomer synthesis of peptoids containing trans -inducing N -imino- and N -alkylamino-glycines
The use of hydrazones as a new type of submonomer in peptoid synthesis is described, giving access to peptoid monomers that are structure-inducing. A wide range of hydrazones were found to readily react with α-bromoamides in routine solid phase peptoid submonomer synthesis. Conditions to promote a one-pot cleavage of the peptoid from the resin and reduction to the corresponding N -alkylamino side chains were also identified, and both the N -imino- and N -alkylamino glycine residues were found to favor the trans -amide bond geometry by NMR, X-ray crystallography, and computational analyses.  more » « less
Award ID(s):
1659690
NSF-PAR ID:
10308951
Author(s) / Creator(s):
 ;  ;  ;  ;  
Date Published:
Journal Name:
Chemical Science
Volume:
12
Issue:
24
ISSN:
2041-6520
Format(s):
Medium: X
Sponsoring Org:
National Science Foundation
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