Simultaneous polymerization and polypeptide particle
Supporting Information
Simultaneous polymerization and polypeptide particle production via reactive spray-drying Lidija Glavas, Karin Odelius, Ann-Christine Albertsson* Fiber and Polymer Technology, School of Chemical Science and Engineering, KTH, Royal Institute of Technology, SE-100 44 Stockholm, Sweden
Results Monomer synthesis The monomers were synthesized by ring-closing of the respective amino-acid derivative, Lglutamic acid
-benzyl ester (Glu), S-benzyl-L-cysteine (Cys), and N-phenyl-p-
phenylenediamine (PhAla) using triphosgene. The reaction solution was heterogeneous from the beginning but after approximately 1 h, it turned homogenous indicating the formation of the N-carboxyanhydride (NCA) as the NCAs have higher solubility in ethyl acetate than the respective amino acid derivative. The NCAs were recrystallized at least three times until pure white crystals were obtained (NCACys formed slightly yellow crystals). The synthesis was performed under an inert atmosphere as well as the purification steps. The NCAs were characterized by 1H-NMR.
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Figure S1. The 1H-NMR of NCAGlu.
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d e e
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Figure S2. The 1H-NMR of NCACys.
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Figure S3. The 1H-NMR of NCAPhAla.
Figure S4. SEC traces of solvent induced polymerization of NCAGlu.
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Figure S5. The 13C NMR spectrum of P(Glu/PhAla) (sample 13).
Figure S6. Particles formed from a monomer feed concentration of 5 mg/mL in THF.
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Figure S7. Particles formed from solely the monomer, with a feed concentration of 2.5 mg/mL in CHCl3.
Figure S8. The morphology of spray-dried PGlu in CHCl3 (monomer feed concentration 2.5 mg/mL).
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Simultaneous polymerization and polypeptide particle production via reactive spray-drying Lidija Glavas, Karin Odelius, Ann-Christine Albertsson* Fiber and Polymer Technology, School of Chemical Science and Engineering, KTH, Royal Institute of Technology, SE-100 44 Stockholm, Sweden
Results Monomer synthesis The monomers were synthesized by ring-closing of the respective amino-acid derivative, Lglutamic acid
-benzyl ester (Glu), S-benzyl-L-cysteine (Cys), and N-phenyl-p-
phenylenediamine (PhAla) using triphosgene. The reaction solution was heterogeneous from the beginning but after approximately 1 h, it turned homogenous indicating the formation of the N-carboxyanhydride (NCA) as the NCAs have higher solubility in ethyl acetate than the respective amino acid derivative. The NCAs were recrystallized at least three times until pure white crystals were obtained (NCACys formed slightly yellow crystals). The synthesis was performed under an inert atmosphere as well as the purification steps. The NCAs were characterized by 1H-NMR.
S1
a
b
c
c
c
d
e f
e d
f
c a
b
c
c
Figure S1. The 1H-NMR of NCAGlu.
b
a
c
d
d e e
c a
8
7
6
5
4
3
2
Figure S2. The 1H-NMR of NCACys.
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b
a
c e
c
c
e c
a
b c
Figure S3. The 1H-NMR of NCAPhAla.
Figure S4. SEC traces of solvent induced polymerization of NCAGlu.
S3
Figure S5. The 13C NMR spectrum of P(Glu/PhAla) (sample 13).
Figure S6. Particles formed from a monomer feed concentration of 5 mg/mL in THF.
S4
Figure S7. Particles formed from solely the monomer, with a feed concentration of 2.5 mg/mL in CHCl3.
Figure S8. The morphology of spray-dried PGlu in CHCl3 (monomer feed concentration 2.5 mg/mL).
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