Building units for N-backbone cyclic peptides .4. Synthesis of protected N-alpha-functionalized alkyl amino acids by reductive alkylation of natural amino acids

被引：31

作者：

Bitan, G ^{[1
]}

Muller, D ^{[1
]}

Kasher, R ^{[1
]}

Gluhov, EV ^{[1
]}

Gilon, C ^{[1
]}

机构：

[1] HEBREW UNIV JERUSALEM,DEPT ORGAN CHEM,IL-91904 JERUSALEM,ISRAEL

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1997年 / 10期

关键词：

D O I：

10.1039/a608389g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method for the synthesis of protected N-alpha-(omega-Y-alkyl) amino acids (Y is a thio, amino or carboxy group) and related compounds by reductive alkylation of natural amino dids is reported, These new amino acids serve as building units for the synthesis of backbone-cyclic peptides, They are orthogonally protected at the alpha-amino position by butoxycarbonyl (Boc) or 9-fluorenylmethoxycarbonyl (Fmoc), using trimethylsilyl temporary protection, to allow for their incorporation into peptides by solid phase peptide synthesis.

引用

页码：1501 / 1510

页数：10

共 50 条

[1] 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):
[2] Building units for N-backbone cyclic peptides .3. Synthesis of protected N-alpha-(omega-aminoalkyl)amino acids and N-alpha-(omega-carboxyalkyl) amino acids
Muller, D
Zeltser, I
Bitan, G
Gilon, C
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (02): : 411 - 416
[3] BUILDING UNITS FOR N-BACKBONE CYCLIC-PEPTIDES .1. SYNTHESIS OF PROTECTED N-(OMEGA-AMINOALKYLENE)AMINO ACIDS AND THEIR INCORPORATION INTO DIPEPTIDE UNITS
BYK, G
GILON, C
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (21): : 5687 - 5692
[4] BUILDING UNITS FOR N-BACKBONE CYCLIC-PEPTIDES .2. SYNTHESIS OF PROTECTED N-(OMEGA-THIOALKYLENE) AMINO-ACIDS AND THEIR INCORPORATION INTO DIPEPTIDE UNITS
BITAN, G
GILON, C
TETRAHEDRON, 1995, 51 (38) : 10513 - 10522
[5] Building Units for N-Backbone Cyclic Peptides. 3. Synthesis of Protected Na-(omega-Aminoalkyl)amino Acids and Na-(omega-Carboxyalkyl)amino Acids
Journal of Organic Chemistry, 62 (02):
[6] Facile synthesis of orthogonally protected amino acid building blocks for combinatorial N-backbone cyclic peptide chemistry
Gellerman, G
Elgavi, A
Salitra, Y
Kramer, I
JOURNAL OF PEPTIDE RESEARCH, 2001, 57 (04): : 277 - 291
[7] Synthesis of novel protected Nα(ω-thioalkyl) amino acid building units and their incorporation in backbone cyclic disulfide and thioetheric bridged peptides
Gazal, S
Gellerman, G
Glukhov, E
Gilon, C
JOURNAL OF PEPTIDE RESEARCH, 2001, 58 (06): : 527 - 539
[8] Conversion of "Customizable Units" into N-Alkyl Amino Acids and Generation of N-Alkyl Peptides
Saavedra, Carlos J.
Carro, Carmen
Hernandez, Dacil
Boto, Alicia
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (13): : 8392 - 8410
[9] SYNTHESIS OF N-ALKYL ALPHA-TRIFLUOROMETHYL ALPHA-AMINO-ACIDS AND INCORPORATION INTO PEPTIDES
BURGER, K
HOLLWECK, W
SYNLETT, 1994, (09) : 751 - 753
[10] Highly practical methodology for the synthesis of D- and L-alpha-amino acids, N-protected alpha-amino acids, and N-methyl-alpha-amino acids
Myers, AG
Gleason, JL
Yoon, T
Kung, DW
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (04) : 656 - 673

← 1 2 3 4 5 →