Synthesis and optimization of tri(propylene glycol) glycerolate diacrylate cross-linked polystyrene resin in polypeptide synthesis: role of the macromolecular support in solid phase peptide synthesis

Sasikumar, Pottayil G.; Kumar, K. Santhosh; Arunan, C.; Pillai, V. N. Rajasekharan

doi:10.1039/b206879f

Cited by 8 publications

(5 citation statements)

References 18 publications

(16 reference statements)

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“…A literature method was followed for synthesizing Chloromethylmethyl Ether (CMME). 8 "Solvents of HPLC grade were bought from E. Merck (India) and BDH (India). A Bruker 300-MSL tool operating on 75.47MHz was used to measure the 13 C NMR measurements.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Biologically Active Peptides using Newly Designed N-Vinyl Pyrrolidone Incorporated Flexible Cross linked Polystyrene

Jacob¹,

Harry²,

Binoj³

et al. 2022

Orient. J. Chem

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Synthesis of NS1 and NS2 peptide fragment of hepatitis C virus polyprotein was carried out on a terpolymer- polystyrene, N-vinylpyrrolidone, 1,6-hexanediol diacrylate resin (PS-NVP-HDDA). The radical aqueous suspension polymerisation resulted in the resin, that exhibited high swelling capacity in various solvents. The peptides were synthesized step-wise by Fmoc strategy, established with amino acid analysis and purified using HPLC. The polymer's high degree of swelling might facilitate free reagent interaction with resin-bound functional sites, resulting in an increased rate of amide bond production. The peptides yield and purity obtained from new support was high when compared to Merrifield resin. These peptides synthesis depicts the application of PS-NVP-HDDA resin developed for synthesis of long chain peptides in high homogeneity and high yield.

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Section: Methodsmentioning

confidence: 99%

Synthesis of Biologically Active Peptides using Newly Designed N-Vinyl Pyrrolidone Incorporated Flexible Cross linked Polystyrene

Jacob¹,

Harry²,

Binoj³

et al. 2022

Orient. J. Chem

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“…131,132 Tri(propylene glycol) glycerolate diacrylate cross-linked polystyrene is another resin reported to show potential as a support for peptide synthesis. 133 Some new protecting group manipulations useful in peptide synthesis have been described. An N α -Alloc protection of a support-bound peptide may be rapidly removed with a mixture of Pd[PPh 3 ] 4 and 1,4-diazabicyclo[2.2.2]octane in the presence of an activated amino acid, enabling an efficient single-step deprotection and coupling.…”

Section: General Methodologymentioning

confidence: 99%

8 Natural polymers—chemistry

Lönnberg

2003

Annu. Rep. Prog. Chem., Sect. B

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“…4 Preparation of HMPA and Rink Linker Functionalized PS-bis(VPP) PEG 400 , Merrifield, and Tentagel Resin HMPA (152 mg, 0.84 mmol) or Fmoc Rink linker (0.453 g, 0.84 mmol), HBTU (318 mg, 0.84 mmol), HOBt (113 mg, 0.84 mmol), and DIEA (144 ll, 0.84 mmol) were added to preswollen amino functionalized 5b resin (1 g, 0.24 mmol) in DMF and the reaction mixture was kept at room temperature for 1 h with occasional swirling. The resin was filtered, washed with DMF (5 3 15 mL), MeOH (5 3 15 mL) and ether (5 3 15 mL), and dried under vacuum.…”

Section: Functional Group Transformationmentioning

confidence: 97%

“…For this the hydroxyl functionalized polymer was treated with SOCl 2 to get chloro-functionalized resin, which was subsequently treated with potassium phthalimide followed by hydrazinolysis to get amino-functionalized resin. 4 The loading capacities of the polymers were determined by Fmoc release assay. The variation in the loading capacity of the polymers 5a, 5b, and 5c with respect to the extent of cross-linking with 4a, 4b, and 4c, respectively, has been tabulated in Table II.…”

mentioning

confidence: 99%

Peptide‐polymer biotherapeutic synthesis on novel cross‐linked beads with “spatially tunable” and “isolated” functional sites

2008

Self Cite

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Solid phase synthesis of polymer biotherapeutics using conventional polymers suffers from many limitations such as low synthetic yield and purity. The conventional polymers prepared by either pre- or post-functionalization strategies have no control over the point of functionalization. Hence we report a novel cross-linked polymer in which the functional groups are spatially tuned to predefined distance with optimal site isolation. This has been achieved by the design and synthesis of a tetra functional PEG, 3,3'-(PEG)bis(1-(4-vinylphenoxy)propan-2-ol) (bis(VPP)PEG). It has been incorporated at cross-linking of 1-12%, into a polystyrene network by free radical suspension polymerization. In this polymer, the distance between hydroxyl functional groups has been spatially tuned in a predefined manner by varying the length of the cross-linker backbone from ethylene glycol to PEG1000 Da and the loading capacity could be varied from 0.1 to 0.9 mmol/g. The polymer has been characterized by SEM, FTIR, and 13C NMR. The polymer exhibits excellent swelling behavior and high chemical stability. The synthetic efficiency of the polymer was demonstrated by the successful synthesis of three structural classes of PEGylated antimicrobial peptide biotherapeutics and the difficult ACP (65-74) fragment. Thus the "spatially defined" and "site isolated" synthesis within the new polymer offers a novel strategy for synthesis of difficult peptide-polymer bioconjugates. The bioassay studies shows that PEGylation of AMPs significantly reduces their hemolytic potential but the retainment of antibacterial property was dependent both on the peptide sequence and the size of PEG used.

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Synthesis and optimization of tri(propylene glycol) glycerolate diacrylate cross-linked polystyrene resin in polypeptide synthesis: role of the macromolecular support in solid phase peptide synthesis

Cited by 8 publications

References 18 publications

Synthesis of Biologically Active Peptides using Newly Designed N-Vinyl Pyrrolidone Incorporated Flexible Cross linked Polystyrene

Synthesis of Biologically Active Peptides using Newly Designed N-Vinyl Pyrrolidone Incorporated Flexible Cross linked Polystyrene

8 Natural polymers—chemistry

Peptide‐polymer biotherapeutic synthesis on novel cross‐linked beads with “spatially tunable” and “isolated” functional sites

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