1,2-Dimethylindole-3-sulfonyl (MIS) as protecting group for the side chain of arginine

被引：10
|
作者：
Isidro, Albert [1 ]
Latassa, Daniel [2 ]
Giraud, Matthieu [2 ]
Alvarez, Mercedes [1 ,3 ,4 ]
Albericio, Fernando [1 ,3 ,5 ]
机构：
[1] Barcelona Sci Pk, Inst Res Biomed, Barcelona 08028, Spain
[2] Lonza AG, TIDES, CH-3930 Visp, Switzerland
[3] Barcelona Sci Pk, Networking Ctr Bioengn Biomat & Nanomed, CIBER BBN, Barcelona 08028, Spain
[4] Univ Barcelona, Fac Pharm, Organ Chem Lab, E-08028 Barcelona, Spain
[5] Univ Barcelona, Dept Organ Chem, E-08028 Barcelona, Spain
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 12期
关键词：
PHASE PEPTIDE-SYNTHESIS; GUANIDINO FUNCTION; ACID; DERIVATIVES; SULFONATION; MECHANISMS; SCAVENGERS; RESIDUES; INDOLE; EDOTN;
D O I：
10.1039/b904836g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The protection of arginine (Arg) side chains is a crucial issue in peptide chemistry because of the propensity of the basic guanidinium group to produce side reactions. Currently, sulfonyl-type protecting groups, such as 2,2,5,7,8-pentamethylchroman (Pmc) and 2,2,4,6,7-pentamethyldihydrobenzofurane (Pbf), are the most widely used for this purpose. Nevertheless, Arg side chain protection remains problematic as a result of the acid stability of these two compounds. This issue is even more relevant in Arg-rich sequences, acid-sensitive peptides and large-scale syntheses. The 1,2-dimethylindole-3-sulfonyl (MIS) group is more acid-labile than Pmc and Pbf and can therefore be a better option for Arg side chain protection. In addition, MIS is compatible with tryptophan-containing peptides.
引用
收藏
页码：2565 / 2569
页数：5
相关论文
共 50 条
  • [31] THE 1ST REPRESENTATIVE OF POLYSILTRIMETHYLENS WITH MESOGENIC GROUP IN SIDE-CHAIN
    USHAKOV, NV
    YARYSHEVA, AY
    TALROZE, RV
    FINKELSHTEIN, ES
    PLATE, NA
    DOKLADY AKADEMII NAUK, 1992, 325 (05) : 964 - 966
  • [32] Synthesis of a series of 3,4-methanoarginines as side-chain conformationally restricted analogues of arginine
    Watanabe, Mizuki
    Yamaguchi, Kazuya
    Tang, Wei
    Yoshida, Keisuke
    Silverman, Richard B.
    Arisawa, Mitsuhiro
    Shuto, Satoshi
    BIOORGANIC & MEDICINAL CHEMISTRY, 2011, 19 (20) : 5984 - 5988
  • [33] 1,2-BIS(SULFONYL)HYDRAZINES .3. EFFECTS OF STRUCTURAL MODIFICATION ON ANTINEOPLASTIC ACTIVITY
    SHYAM, K
    HRUBIEC, RT
    FURUBAYASHI, R
    COSBY, LA
    SARTORELLI, AC
    JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (11) : 2157 - 2161
  • [34] Preparation of free-standing films with sulfonyl group from 3-mercaptopropyl(trimethoxy)silane/1,2-bis(triethoxysilyl)ethane copolymer
    Gunji, Takahiro
    Shigematsu, Yasunobu
    Kajiwara, Takashi
    Abe, Yoshimoto
    POLYMER JOURNAL, 2010, 42 (08) : 684 - 688
  • [35] PARTICLE FLUID INTERACTIONS WITH APPLICATIONS TO SOLID-STABILIZED EMULSIONS .3. ASPHALTENE ADSORPTION IN THE PRESENCE OF QUINALDINE AND 1,2-DIMETHYLINDOLE
    MENON, VB
    WASAN, DT
    COLLOIDS AND SURFACES, 1987, 23 (04): : 353 - 362
  • [36] Preparation of free-standing films with sulfonyl group from 3-mercaptopropyl(trimethoxy)silane/1,2-bis(triethoxysilyl)ethane copolymer
    Takahiro Gunji
    Yasunobu Shigematsu
    Takashi Kajiwara
    Yoshimoto Abe
    Polymer Journal, 2010, 42 : 684 - 688
  • [37] High relative dielectric constants poly(3-alkylthiophene)s from side chain modification with sulfoxide and sulfonyl groups
    Wang, Chunlai
    Zhang, Zhongbo
    Zhu, Lei
    Sauve, Genevieve
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 256
  • [38] PHOTOISOMERIZATION OF 1,2-DIPHENYLCYCLOPROPANE SENSITIZED BY POLYPEPTIDES CONTAINING NAPHTHALENE GROUPS IN THEIR SIDE-CHAIN
    UENO, A
    TODA, F
    IWAKURA, Y
    JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY, 1974, 12 (08) : 1841 - 1849
  • [39] Characteristics of the amorphous polyvinyl alcohol resin derivative having side chain 1,2-diol
    Shibutani, Mitsuo
    Kanda, Taiji
    Yamamoto, Tomoyuki
    Tokumitsu, Katsuhisa
    Zairyo/Journal of the Society of Materials Science, Japan, 2017, 66 (01): : 23 - 28
  • [40] SYNTHESIS OF 1-VINYLCYCLOPROPANES AND 1,2-DIVINYLCYCLOPROPANES CONTAINING FUNCTIONAL GROUPS IN SIDE-CHAIN OR IN RING
    YANOVSKA.LA
    DOMBROVS.VA
    KUCHEROV, VF
    IZVESTIYA AKADEMII NAUK SSSR-SERIYA KHIMICHESKAYA, 1974, (04): : 901 - 903
12345