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- W1970657784 abstract "A model peptide with the sequences Ala‐Pro‐Lys(2ClZ)‐Tyr(2BrZ) was synthesized on a 4‐methylbenzhydryl amine (MBHA) polystyrene resin using conventional Boc/benzyl protective group strategy. The amino acid aldehyde Boc‐valinal was coupled by reductive alkylation with NaCNBH 3 in acidified DMF for 1 h. The secondary amine in the peptide‐resin Boc‐Valψ[CH 2 NH]Ala‐Pro‐Lys(2CIZ)‐Tyr(2BrZ)‐MBHA was reductively alkylated by 3(4‐methylbenzylthio)‐propanal at 40 °C for 6 h, resulting the peptide‐resin Boc‐Valψ[CH 2 N(CH 2 CH 2 CH 2 ‐S‐pMeBzl)]Ala‐Pro‐Lys(2ClZ)‐Tyr(2BrZ)‐MBHA. After the removal of the Boc group the synthesis was continued employing the above‐mentioned methods, which led to the resin‐bound peptide Leuψ[CH 2 N(CH 2 CH 2 CH 2 S‐pMeBzl)]Ser‐Pro‐Gly‐Lys(2ClZ)‐Valψ[CH 2 N(CH 2 CH 2 CH 2 ‐S‐pMeBzl)]Ala‐Pro‐Lys(2ClZ)‐Tyr(2BrZ)‐MBHA. The peptide was cleaved from the resin with hydrogen fluoride. Reversed‐phase HPLC and plasma desorbtion mass spectrometry analysis showed that the expected peptide Leuψ[CHIN(CH 2 CH 2 CH 2 SH)ISer‐Pro‐Gly‐Lys‐Valψ[CH 2 N(CH 2 CH 2 CH 2 ‐SH)]Ala‐Pro‐Lys‐Tyr‐NH 2 was obtained as the major product with low levels of side products. Intramolecular oxidation of the thiols gave the backbone to backbone cyclized peptide Leuψ[CH 2 N(CH 2 CH 2 CH 2 S)]Ser‐Pro‐Gly‐Lys‐Valψ[CH 2 N(CH 2 CH 2 CH 2 ‐S)]A1a‐Pro‐Lys‐Tyr‐NH 2 ." @default.
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- W1970657784 date "1994-05-01" @default.
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- W1970657784 title "A new general solid-phase method for the synthesis of backbone-to-backbone cyclized peptides" @default.
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- W1970657784 doi "https://doi.org/10.1111/j.1399-3011.1994.tb00550.x" @default.
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