Side Reaction with N-Carboxymethyl Amino Acids in the Synthesis of Backbone Cyclized Peptides

被引：0
|
作者：
Diana Besser
Georg Greiner
Siegmund Reissmann
机构：
[1] Friedrich-Schiller-Universität Jena,Institut für Biochemie und Biophysik
来源：
Letters in Peptide Science | 1998年 / 5卷 / 4期
关键词：
backbone cyclization; bradykinin; branched building units; diketopiperazine formation;
D O I：
10.1023/A:1008806304435
中图分类号：
学科分类号：
摘要：
The use of N-carboxymethyl amino acids in the assembly of peptides with backbone cyclization can lead to diketopiperazine formation by intramolecular aminolysis which occurs despite the tert-butyl protection of the carboxy group. This undesired side reaction can be prevented by a very short deprotection time for the Fmoc group, by elongation of the N-carboxyalkyl chain or by forming the backbone (lactam) bridge before Fmoc removal, but not by the use of DBU or additives.
引用
收藏
页码：299 / 303
页数：4
相关论文
共 50 条
  • [41] Synthesis of new β2,2-amino acids with carbohydrate side chains: impact on the synthesis of peptides
    Sharma, Gangavaram V. M.
    Rajender, Karnekanti
    Sridhar, Gattu
    Reddy, Post Sai
    Kanakaraju, Marumudi
    CARBOHYDRATE RESEARCH, 2014, 388 : 8 - 18
  • [42] PEPTIDES SYNTHESIS - COUPLING OF PENTACHLOROPHENYL ACTIVE ESTERS OF N-CARBOBENZOXY AMINO ACIDS AND PEPTIDES TO PENTACHLOROPHENYL ACTIVE ESTER HYDROCHLORIDES OF AMINO ACIDS
    KAPOOR, A
    JOURNAL OF PHARMACEUTICAL SCIENCES, 1967, 56 (11) : 1532 - &
  • [43] Synthesis and in vitro evaluation of methotrexate conjugated O,N-carboxymethyl chitosan via peptidyl spacers
    Dan Li
    Bo Lu
    Hong Zhang
    Zhijun Huang
    Peihu Xu
    Hua Zheng
    Yihua Yin
    Haixing Xu
    Xia Liu
    Yiceng Lou
    Xueqiong Zhang
    Fuliang Xiong
    Journal of Nanoparticle Research, 2014, 16
  • [44] SYNTHESES OF N-CARBOXYMETHYL DIPEPTIDES VIA N-CARBOXY ALPHA-AMINO-ACID ANHYDRIDES (NCA) INTERMEDIATES
    SKILES, JW
    WARUS, JD
    SUH, JT
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 1988, 20 (1-2) : 109 - 115
  • [45] THE SYNTHESIS OF SIMPLE PEPTIDES FROM ANHYDRO-N-CARBOXY-AMINO-ACIDS
    BAILEY, JL
    JOURNAL OF THE CHEMICAL SOCIETY, 1950, (DEC): : 3461 - 3466
  • [46] SYNTHESIS OF ADENYLYL-(5' -]N) - AMINO ACIDS (PEPTIDES) BY CARBODIIMIDE METHOD
    RYABOVA, TS
    SHABAROV.ZA
    PROKOFEV, MA
    BIOCHEMISTRY-MOSCOW, 1965, 30 (02) : 201 - &
  • [47] Synthesis and conformation of backbone N-aminated peptides
    Rathman, Benjamin M.
    Rowe, Jennifer L.
    Del Valle, Juan R.
    SYNTHETIC AND ENZYMATIC MODIFICATIONS OF THE PEPTIDE BACKBONE, 2021, 656 : 271 - 294
  • [48] N-MALEYL-AMINO ACIDS AND PEPTIDES
    AUGUSTIN, M
    MULLER, W
    ZEITSCHRIFT FUR CHEMIE, 1985, 25 (01): : 18 - 19
  • [49] Building units for N-backbone cyclic peptides. Part 4. Synthesis of protected Na-functionalized alkyl amino acids by reductive alkylation of natural amino acids
    Bitan, G.
    Muller, D.
    Kasher, R.
    Gluhov, E. V.
    Jornal of the Chemical Society. Perkin Transactions 1, (10):
  • [50] Synthesis of neoglygopeptides by chemoselective reaction of carbohydrates with peptides containing novel N′-methyl-aminooxy amino acids.
    Carrasco, MR
    Nguyen, MJ
    Sasikumar, VA
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U118 - U118
12345