Beilstein J. Org. Chem.2025,21, 47–54, doi:10.3762/bjoc.21.5
functionalities of naturally occurring amino acids, synthetic polypeptides offer a robust platform for designing drug delivery systems that meet the criteria of biodegradability and biocompatibility [13]. The present study focuses on a polysarcosine and poly-ʟ-(benzyl glutamate) block copolymer (PSar-PBLG), as it
would improve the effectivity of the osmotic pressure applied up to a certain point, after which the membrane would be too rigid for deformation. Within this window it is expected that stomatocytes could be obtained using PSar-PBLG block copolymers.
Results and Discussion
Starting with the synthesis of
the PSar-PBLG that was used for all the following systems, it was found that a polymer with a length of 50 units sarcosine and 40 units benzyl glutamate would be able to form vesicles between 300–700 nm (Supporting Information File 1, Figure S22). The synthesis of PSar-PBLG (Scheme 1) involved anionic
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Graphical Abstract
Scheme 1:
i) Synthesis of benzyl glutamate NCA using phosgene and propylene oxide as a scavenger. ii) Ring-op...
Beilstein J. Org. Chem.2018,14, 106–113, doi:10.3762/bjoc.14.6
demonstrated that both associative and dissociative pathways operate to varying degrees, according to the nature of the nucleophile and the hydrogen bond donor.
Keywords: benzylic fluorides; C–F activation; chiral liquid crystal; 2H NMR; PBLG; stereochemistry; Introduction
The C–F bond is the strongest
with the electric field gradients associated with the orientated media, creating anisotropy and resolving into two sets of doublets. If there is sufficient resolution between these quadrupolar couplings, then the enantiomeric ratio can be recorded. We have used poly-γ-benzyl-L-glutamate (PBLG
reduced under Noyori’s conditions [12] using (S,S)-Ru(DPEN)2 as catalyst and [2H2]-formic acid as the deuterium source. This afforded the corresponding 7-[2H1]-(S)-benzyl alcohol ((S)-3) in moderate yield (81%) and high ee (95%), as evidenced by 2H-PBLG-NMR. Benzyl alcohol 3 was converted to the
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Graphical Abstract
Figure 1:
C–F activation of benzylic fluorides to generate benzylamine or diarylmethane products.