First synthesis of a fully active spin‐labeled peptide hormone 1

FEBS Letters

Castrucci, Ana Maria L²  Cilli, Eduardo M¹  Nakaie, Clovis R¹  Lamy-Freund, M.Teresa³  Barbosa, Simone R¹ 

[1] Departamento de Biofı́sica, Universidade Federal de São Paulo, Rua 3 de Maio 100, CEP 04044-020, São Paulo, SP, Brazil;Departamento de Fisiologia, Instituto de Biociências, Universidade de São Paulo, CP 11176, São Paulo, SP, Brazil;Instituto de Fı́sica, Universidade de São Paulo, CP 66318, São Paulo, SP, Brazil

关键词: Spin-labeled peptide;    α-Melanocyte stimulating hormone;    Electron spin resonance;    Skin pigmentation;    Boc;    tert-butyloxycarbonyl;    Bzl;    benzyl;    C18;    octadecyl;    2-BrZ;    2-bromobenzyloxycarbonyl;    2-ClZ;    2-chlorobenzyloxycarbonyl;    OcHex;    cyclohexyl;    For;    formyl;    Tos;    p-toluenesulfonyl;    Ac;    acetyl;    DCM;    dichloromethane;    DIEA;    N;    N-diisopropylethylamine;    DMF;    N;    N-dimethylformamide;    DMS;    dimethylsulphide;    EDT;    ethanedithiol;    Fmoc;    9-fluorenylmethyloxycarbonyl;    TBTU;    2-(1H-benzotriazole-1-yl)-1;    1;    3;    3-tetramethyluronium tetrafluoroborate;    HOBt;    1-hydroxybenzotriazole;    HPLC;    high performance liquid chromatography;    MeCN;    acetonitrile;    MBHAR;    methylbenzohydrylamine-resin;    NMP;    1-methyl-2-pyrrolidinone;    TFA;    trifluoroacetic acid;    Toac;    2;    2;    6;    6-tetramethylpiperidine-1-oxyl-4-amino-4-carboxylic acid;   

DOI  :  10.1016/S0014-5793(99)00172-6

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

For the first time in the electron spin resonance (ESR) and peptide synthesis fields, a fully active spin-labeled peptide hormone was reported. The ESR spectra of this α-melanocyte stimulating hormone (α-MSH) analogue (acetyl-Toac⁰-α-MSH) where Toac is the paramagnetic amino acid probe 2,2,6,6-tetramethylpiperidine-1-oxyl-4-amino-4-carboxylic acid, suggested a pH-independent conformation and a more restricted movement comparatively to the free Toac. Owing to its equivalent biological potency in a skin pigmentation assay as compared to the native α-MSH and its unique characteristic (paramagnetic, naturally fluorescent and fully active), this analogue is of great potential for investigation of relevant physiological roles reported for α-MSH.

【 授权许可】

Unknown