RACEMIZATION-FREE SYNTHESIS OF C-TERMINAL CYSTEINE-PEPTIDE USING 2-CHLOROTRITYL RESIN

被引：0
|
作者：
FUJIWARA, Y [1 ]
AKAJI, K [1 ]
KISO, Y [1 ]
机构：
[1] KYOTO PHARMACEUT UNIV, DEPT MED CHEM, YAMASHINA KU, KYOTO 607, JAPAN
来源：
CHEMICAL & PHARMACEUTICAL BULLETIN | 1994年 / 42卷 / 03期
关键词：
SOLID PHASE PEPTIDE SYNTHESIS; RACEMIZATION; C-TERMINAL CYSTEINE; BASE TREATMENT; 2-CHLOROTRITYL RESIN; SOMATOSTATIN;
D O I：
暂无
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
We investigated the effects of bases, resins, and S-protecting groups on the extent of racemization at the C-terminal cysteine during Fmoc-based(Fmoc=fluoren-9-yl-methoxy-carbonyl) solid phase peptide synthesis. The use of 2-chlorotrityl resin was most effective in suppressing the racemization caused by the base treatment for Fmoc-cleavage. Somatostatin was successfully synthesized with practically no racemization using 2-chlorotrityl resin by Fmoc-chemistry.
引用
收藏
页码：724 / 726
页数：3
相关论文
共 50 条
  • [31] Ethyl 2-(tert-Butoxycarbonyloxyimino)-2-cyanoacetate (Boc-Oxyma) as Coupling Reagent for Racemization-Free Esterification, Thioesterification, Amidation and Peptide Synthesis
    Thalluri, Kishore
    Nadimpally, Krishna Chaitanya
    Chakravarty, Maharishi Parasar
    Paul, Ashim
    Mandal, Bhubaneswar
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (2-3) : 448 - 462
  • [32] ADVANCES IN ULTRAHIGH LOAD POLYMER-SUPPORTED PEPTIDE-SYNTHESIS WITH PHENOLIC SUPPORTS .2. USE OF HYDRAZINOLYSIS-HPLC TO CHECK FOR RACEMIZATION ON C-TERMINAL AMINO-ACID LOADING AND TO DETERMINE PEPTIDE HOMOGENEITY DURING SYNTHESIS WITH SELECTIVELY LABILE C-TERMINAL ANCHORING LINKAGES
    BAKER, PA
    COFFEY, AF
    EPTON, R
    JOHNSON, T
    MOLE, EJ
    MAKROMOLEKULARE CHEMIE-MACROMOLECULAR SYMPOSIA, 1988, 19 : 79 - 91
  • [33] Ethyl 2-Cyano-2-(2-nitrobenzenesulfonyloxyimino)acetate (o-NosylOXY): A Recyclable Coupling Reagent for Racemization-Free Synthesis of Peptide, Amide, Hydroxamate, and Ester
    Dev, Dharm
    Palakurthy, Nani Babu
    Thalluri, Kishore
    Chandra, Jyoti
    Mandal, Bhubaneswar
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (12): : 5420 - 5431
  • [34] O-to-O acyl transfer for epimerization-free peptide C-terminal salicylaldehyde ester synthesis
    Xia, Wang
    Li, Bing-Wen
    Zhong, Zhixiang
    Liu, Jiamei
    Liu, Han
    Yu, Zhi-Xiang
    Li, Xuechen
    NATURE SYNTHESIS, 2024, 3 (08): : 1049 - 1060
  • [35] SYNTHESIS OF C-TERMINAL TETRAPEPTIDE AMIDE OF OXYTOCIN SERIES USING THE DIFFERENT PROTECTIVE GROUPS OF THE THIOL FUNCTION OF CYSTEINE
    IVANOV, AK
    GRIGOREVA, EE
    ANTONOV, AA
    DONETSKII, IA
    KHIMIYA PRIRODNYKH SOEDINENII, 1992, (3-4): : 400 - 406
  • [36] Racemization-Free Chemoenzymatic Peptide Synthesis Enabled by the Ruthenium-Catalyzed Synthesis of Peptide Enol Esters via Alkyne-Addition and Subsequent Conversion Using Alcalase-Cross-Linked Enzyme Aggregates
    Schroeder, Hilmar
    Strohmeier, Gernot A.
    Leypold, Mario
    Nuijens, Timo
    Quaedflieg, Peter J. L. M.
    Breinbauer, Rolf
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (09) : 1799 - 1807
  • [37] Improved synthesis of C-terminal peptide thioesters on "safety-catch" resins using LiBr/THF
    Quaderer, R
    Hilvert, D
    ORGANIC LETTERS, 2001, 3 (20) : 3181 - 3184
  • [38] On resin preparation of C-terminal peptide amides, analogs of the nematode neuropeptide PF1, SDPNFLRF-NH2, by application of a cysteine-specific precursor cleavage
    Kubiak, TM
    Friedman, AR
    Larsen, MJ
    PEPTIDES: FRONTIERS OF PEPTIDES SCIENCE, 1999, : 327 - 328
  • [39] Fmoc-based solid-phase peptide synthesis using Dpr(Phoc) linker. Synthesis of a C-terminal proline peptide
    Sola, R
    Mery, J
    Pascal, R
    TETRAHEDRON LETTERS, 1996, 37 (51) : 9195 - 9198
  • [40] Racemization free longer N-terminal peptide hydroxamate synthesis on solid support using ethyl 2-(tert-butoxycarbonyloxyimino)-2-cyanoacetate
    Manne, Srinivasa Rao
    Thalluri, Kishore
    Giri, Rajat Subhra
    Paul, Ashim
    Mandal, Bhubaneswar
    TETRAHEDRON LETTERS, 2015, 56 (44) : 6108 - 6111
12345