Carbonyldiimidazole (CDI) Mediated Synthesis of Nα-Protected Amino Acid Azides: Application to the One-pot Preparation of Ureidopeptides

被引:2
|
作者
Vasantha, B. [1 ]
Vishwanatha, T. M. [1 ]
Sureshbabu, Vommina V. [1 ]
机构
[1] Bangalore Univ, Dept Studies Chem, Peptide Res Lab, Bangalore 560001, Karnataka, India
来源
PROTEIN AND PEPTIDE LETTERS | 2011年 / 18卷 / 11期
关键词
Acyl azide; CDI; one-pot reaction; ureidopeptides; PROTEASE INHIBITORS; PEPTIDE ISOCYANATES; ACYL AZIDES; UREAS; PEPTIDOMIMETICS; DERIVATIVES; CONVERSION; CATALYSIS; CONCISE;
D O I
10.2174/092986611797200922
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Synthesis of N-alpha-protected amino acyl azides starting from corresponding acids via the carbonyldiimidazole (CDI) activation is described. The protocol is extended for a one-pot preparation of ureido peptides that circumvents the isolation of acyl azide and isocyanate intermediates. The reaction was accomplished without using any additives and base. The protocol is simple, clean, high yielding and free from racemization.
引用
收藏
页码:1093 / 1098
页数:6
相关论文
共 50 条
  • [21] One-Pot Synthesis of Nα-Protected Amino/Peptide O-benzyl Hydroxamates and Acylaminoxy Dipeptides Employing Hydroxamic Acid
    Krishnamurthy, Muniyappa
    Sagar, N. R.
    Sureshbabu, Vommina V.
    INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS, 2017, 23 (02) : 191 - 197
  • [22] One-Pot Synthesis of Nα-Protected Amino/Peptide O-benzyl Hydroxamates and Acylaminoxy Dipeptides Employing Hydroxamic Acid
    Muniyappa Krishnamurthy
    N. R. Sagar
    Vommina V. Sureshbabu
    International Journal of Peptide Research and Therapeutics, 2017, 23 : 191 - 197
  • [23] 'One-pot' synthesis of chiral N-protected α-amino acid-derived 1,2,4-oxadiazoles
    Braga, AL
    Lüdtke, DS
    Alberto, EE
    Dornelles, L
    Filho, WAS
    Corbellini, VA
    Rosa, DM
    Schwab, RS
    SYNTHESIS-STUTTGART, 2004, (10): : 1589 - 1594
  • [24] One-pot synthesis of orthogonally protected dipeptide selenazoles employing Nα-amino selenocarboxamides and α-bromomethyl ketones
    Madhu, Chilakapati
    Panguluri, Nageswara Rao
    Narendra, N.
    Panduranga, V.
    Sureshbabu, Vommina V.
    TETRAHEDRON LETTERS, 2014, 55 (50) : 6831 - 6835
  • [25] TFAA mediated one-pot synthesis of chiral N-protected amino acid-derived 1,2,4-oxadiazoles and their antibacterial studies
    Saravanakumar, Srinivasan Pon
    Nagasundaram, Nagarajan
    Dhineshkumar, Jayaraman
    Rajalakshmi, Periyaswamy
    Lalitha, Appaswami
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2025, 23 (02) : 360 - 368
  • [26] CuI-Promoted One-Pot Synthesis of N-Boc Protected β-Ketotriazole Amino Acids: Application in the Synthesis of New Class of Dipeptidomimetics
    Vishwanatha, T. M.
    Narendra, N.
    Sureshbabu, Vommina V.
    PROTEIN AND PEPTIDE LETTERS, 2012, 19 (03): : 308 - 314
  • [27] One-Pot Conversion of Benzyl Alcohols to N-Protected Anilines and Alkyl Alcohols to Carbamoyl Azides
    Kobayashi, Shoji
    Yamaguchi, Ryo
    Yamamoto, Fumiya
    Komori, Jun
    Sakamoto, Hotaka
    Kasashima, Takahiro
    Adriaenssens, Louis
    Lear, Martin J.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 26 (47)
  • [28] A novel, one-pot preparation of N-methyl-α-amino acid dipeptides from oxazolidinones and amino acids
    Dorow, RL
    Gingrich, DE
    TETRAHEDRON LETTERS, 1999, 40 (03) : 467 - 470
  • [29] A one-pot preparation of N-2-mercaptobenzoyl-amino amides
    Bande, Robert J.
    Appella, Daniel H.
    Trenkle, William C.
    TETRAHEDRON LETTERS, 2011, 52 (32) : 4103 - 4105
  • [30] One-Pot Synthesis of Functionalized α-Acyloxythioamides from N-Protected α-Amino Acids as an Acid Component in the Passerini Reaction in an Ionic Liquid
    Yavari, I.
    Shahvelayati, A. S.
    Ghanbari, M.
    Ghazvini, M.
    Piltan, M.
    JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2011, 8 (03) : 636 - 642