An efficient method for the preparation of peptide alcohols

被引:13
作者
Katritzky, Alan Roy [1 ]
Abo-Dya, Nader Elmaghwry [1 ,2 ]
Tala, Srinivasa Rao [1 ]
Gyanda, Kapil [1 ]
Abdel-Samii, Zakaria Kamel [2 ]
机构
[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA
[2] Zagazig Univ, Fac Pharm, Dept Organ Pharmaceut Chem, Zagazig 44519, Egypt
关键词
ASYMMETRIC TRANSFER-HYDROGENATION; AMINO-ACIDS; ALDEHYDES; CONVENIENT; DIPEPTIDES; LIGANDS; FMOC-ALPHA-AMINOACYL)BENZOTRIAZOLES; DERIVATIVES; REDUCTION; ACYLATION;
D O I
10.1039/b905730g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Protected LL-dipeptide alcohols 3a-p, diastereomeric mixture (3d + 3d') and tripeptide alcohols 6a-c were synthesized by treatment of various amino alcohols with N-protected(alpha-aminoacyl)benzotriazoles 1a-c, 1f-m, (1a + 1a') and N-protected(alpha-dipeptidoyl) benzotriazoles 5a, 5b respectively in good yields with complete retention of chirality.
引用
收藏
页码:4444 / 4447
页数:4
相关论文
共 39 条
[1]   Investigation into the P3 binding domain of m-calpain using photoswitchable diazo- and triazene-dipeptide aldehydes:: New anticataract agents [J].
Abell, Andrew D. ;
Jones, Matthew A. ;
Neffe, Axel T. ;
Aitken, Steven G. ;
Cain, Thomas P. ;
Payne, Richard J. ;
McNabb, Stephen B. ;
Coxon, James M. ;
Stuart, Blair G. ;
Pearson, David ;
Lee, Hannah Y. -Y. ;
Morton, James D. .
JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (12) :2916-2920
[2]   GLYCYLCYCLINES .3. 9-AMINODOXYCYCLINECARBOXAMIDES [J].
BARDEN, TC ;
BUCKWALTER, BL ;
TESTA, RT ;
PETERSEN, PJ ;
LEE, VJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (20) :3205-3211
[3]   A new type of ligand derived from N-terminal protected dipeptides in enantioselective addition of phenylacetylene to aromatic ketones at room temperature [J].
Cai, Hua-qing ;
Chen, Chao ;
Liu, Lei ;
Ni, Jing-man ;
Wang, Rui .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 253 (1-2) :86-91
[4]   Highly stereoselective conversion of aryl peptidyl ketones into the corresponding peptide alcohols [J].
Di Gioia, ML ;
Leggio, A ;
Le Pera, A ;
Liguori, A ;
Siciliano, C .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (03) :463-467
[5]   Solid-phase synthesis of phosphine-oxazoline peptides [J].
Gilbertson, SR ;
Lan, P .
TETRAHEDRON LETTERS, 2002, 43 (39) :6961-6965
[6]   Vanadium(II)- and niobium(III)-induced, diastereoselective pinacol coupling of peptide aldehydes to give a C-2-symmetrical HIV protease inhibitor [J].
Kammermeier, B ;
Beck, G ;
Holla, W ;
Jacobi, D ;
Napierski, B ;
Jendralla, H .
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (03) :307-315
[7]   N-Fmoc-protected(α-dipeptidoyl)benzotriazoles for efficient solid-phase peptide synthesis by segment condensation [J].
Katritzky, Alan R. ;
Yoshioka, Megumi ;
Narindoshvili, Tamari ;
Chung, Alfred ;
Khashab, Niveen M. .
CHEMICAL BIOLOGY & DRUG DESIGN, 2008, 72 (03) :182-188
[8]   Microwave-assisted solid-phase peptide synthesis utilizing N-Fmoc-Protected (α-aminoacyl)benzotriazoles [J].
Katritzky, Alan R. ;
Khashab, Niveen M. ;
Yoshioka, Megumi ;
Haase, Danniebelle N. ;
Wilson, Krista R. ;
Johnson, Jodie V. ;
Chung, Alfred ;
Haskell-Luevano, Carrie .
CHEMICAL BIOLOGY & DRUG DESIGN, 2007, 70 (05) :465-468
[9]   One-carbon homologation of aldehydes to N-(α-haloacyl)benzotriazoles [J].
Katritzky, Alan R. ;
Tala, Srinivasa R. ;
Singh, Sandeep K. .
SYNTHESIS-STUTTGART, 2006, (19) :3231-3237
[10]   Efficient Synthesis of Azo Dye Labeled Terpenes, Sugars, and Steroids Using N-(4-Arylazobenzoyl)-1H-benzotriazoles [J].
Katritzky, Alan R. ;
Tala, Srinivasa R. ;
Abo-Dya, Nader E. ;
Abdel-Samii, Zakaria K. .
SYNTHESIS-STUTTGART, 2009, (10) :1708-1714