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Synthesis of Protected Tetrapeptide, N-o-Ns-N(Me)-Val-N(Me)-Val-N(Me)-Val-N(Me)-Phe-O^tBu

Synthesis of Protected Tetrapeptide, N-o-Ns-N(Me)-Val-N(Me)-Val-N(Me)-Val-N(Me)-Phe-O^tBu
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摘要 The protected tetrapeptide, N-o-Ns-N ( Me ) -Val-N ( Me ) -Val-N ( Me ) -Val- N ( Me ) -Phe- OtBu, was prepared from L-valine and L-phenylalanine. Ted-butyl acetate and HClO4 were used to protect carbonyl group, o-nitrobenzenesulfonyl chloride and triethyl amine were used to protect amino group, and N-alkylation was finished with iodomethane. Then the protected amino acid was turned into acid chloride which was taken as coupling reagent. After 14 steps, such as protection, alkylation, deprotection and coupling, the protected tetrapeptide was obtained with a yield of 26.9%. The structures of intermediates and target compound were identified with NMR spectra and high resolution mass spectra. The protected tetrapeptide, N-o-Ns-N(Me)-Val-N(Me)-Val-N(Me)-Val- N(Me)-Phe-OtBu, was prepared from L-valine and L-phenylalanine. Tert-butyl acetate and HClO4 were used to protect carbonyl group, o-nitrobenzenesulfonyl chloride and triethyl amine were used to protect amino group, and N-alkylation was finished with iodomethane. Then the protected amino acid was turned into acid chloride which was taken as coupling reagent. After 14 steps, such as protection, alkylation, deprotection and coupling, the protected tetrapeptide was obtained with a yield of 26.90/0. The structures of intermediates and target compound were identified with NMR spectra and high resolution mass spectra.
出处 《Transactions of Tianjin University》 EI CAS 2006年第5期364-368,共5页 天津大学学报(英文版)
关键词 synthesis TETRAPEPTIDE L-VALINE L-PHENYLALANINE 四肽 合成 L-缬氨酸 L-苯基丙氨酸
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  • 1Yvonne M.Angell, Carlos Garcia-Echeverria, aniel H.Rich, Comparative Studies of the Coupling of N-Methylated, Sterically Hindered mino Acids During Solid-Phase Peptide Synthesis[].Tetrahedron Letters.1994 被引量:1
  • 2George R Pettit,Yoshiaki Kamano,Cherry L Herald et al.Structure of bryostatin4: An important antineo- plastic constituent of geographically diverseBugula neritina[ J][].Journal of the American Chemical Society.1984 被引量:1
  • 3Jorge I Jim啨nez,Paul J Scheuer.New lipopeptides from the Caribbean CyanobacteriumLyngbya majuscu- la. JNat Prod . 2001 被引量:1
  • 4Akaji K,Hayashi Y,Kiso Y.Convergent synthesis of dolastatin 15 by solid phase coupling of N-methylami- no acid[].JOrg Chem.1999 被引量:1
  • 5Rodney L Parsons,Clayton H Heathcock.Total syn- thesis of mirabazole B[].Tetrahedron Letters.1994 被引量:1
  • 6Hu J,Miller MJ.Total synthesis of a mycobactin S, a siderophore and growth promoter of mycobacterium smegmatis, and determination of its growth inhibitory activity against mycobacterium tuberculosis[].Journal of the American Chemical Society.1997 被引量:1
  • 7Oliver Seitz.New protecting group strategies for the solid-phase synthesis and modification of peptides, ol- igonucleotides, and oligosaccharides [ J][].Angewandte Chemie International Edition.1998 被引量:1
  • 8Injae Shin,Kisoo Park.Solution-phase synthesis of aminooxy peptoids in the C to Nand Nto C directions[].Organic Letters.2002 被引量:1
  • 9Edwin Vedejs,Chutima Kongkittingam.Solution- phase synthesis of a hindered N-methylated tetrapep- tide using Bts-protected amino acid chlorides: Effi- cient coupling and methylation steps allowing purifi- cation by extraction[].Journal of Organic Chemistry.2000 被引量:1

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