α,β-Dehydroamino Acid Synthesis through Proline-Catalyzed Aldol Condensation with a Glycine Schiff Base

被引：1

作者：

Sawamura, Jun ^{[1
]}

Ieiri, Daikan ^{[1
]}

Yazaki, Ryo ^{[1
]}

Ohshima, Takashi ^{[1
]}

机构：

[1] Kyushu Univ, Grad Sch Pharmaceut Sci, Fukuoka 8128582, Japan

来源：

PRECISION CHEMISTRY | 2023年 / 2卷 / 01期

基金：

日本科学技术振兴机构;

关键词：

alpha; beta-dehydroamino acid; peptide; proline; aldol condensation; glycine Schiff base; transimination; ALPHA-AMINO-ACIDS; PHASE-TRANSFER CATALYSIS; ROBUSTNESS SCREEN; PEPTIDE-SYNTHESIS; IMINE METATHESIS; EFFICIENT METHOD; TRANSIMINATION; ALDEHYDES; ESTERS; DERIVATIVES;

D O I：

10.1021/prechem.3c00048

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general protocol for the synthesis of alpha,beta-dehydroamino acids and their peptides was developed. Proline efficiently catalyzed an aldol condensation reaction of a glycine Schiff base with a variety of aldehydes. The hydroxy group on the benzophenone imine was crucial for high Z/E selectivity and further transimination for protecting group-free alpha,beta-dehydroamino esters. Peptide elongation of both the C- and N-terminals highlighted the usefulness of our present protocol.

引用

页码：14 / 20

页数：7

共 72 条

[31] Elucidation and Total Synthesis of the Correct Structures of Tridecapeptides Yaku'amides A and B. Synthesis-Driven Stereochemical Reassignment of Four Amino Acid Residues [J].

Kuranaga, Takefumi ;

Mutoh, Hiroyuki ;

Sesoko, Yusuke ;

Goto, Tomomi ;

Matsunaga, Shigeki ;

Inoue, Masayuki .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (29) :9443-9451

[32] Total Synthesis and Complete Structural Assignment of Yaku'amide A [J].

Kuranaga, Takefumi ;

Sesoko, Yusuke ;

Sakata, Komei ;

Maeda, Naoya ;

Hayata, Atsushi ;

Inoue, Masayuki .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5467-5474

[33] Cyclizing Pentapeptides: Mechanism and Application of Dehydrophenylalanine as a Traceless Turn-Inducer [J].

Le, Diane N. ;

Riedel, Jan ;

Kozlyuk, Natalia ;

Martin, Rachel W. ;

Dong, Vy M. .

ORGANIC LETTERS, 2017, 19 (01) :114-117

[34] Characterization and Utility of N-Unsubstituted Imines Synthesized from Alkyl Azides by Ruthenium Catalysis [J].

Lee, Jin Hee ;

Gupta, Sreya ;

Jeong, Wook ;

Rhee, Young Ho ;

Park, Jaiwook .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (43) :10851-10855

[35]

Li MY, 2017, NAT CHEM, V9, P997, DOI [10.1038/NCHEM.2760, 10.1038/nchem.2760]

[36] Asymmetric phase-transfer catalysis utilizing chiral quaternary ammonium salts: Asymmetric alkylation of glycine imines [J].

Lygo, B ;

Andrews, BI .

ACCOUNTS OF CHEMICAL RESEARCH, 2004, 37 (08) :518-525

[37] Enantioselective amino acid synthesis by chiral phase-transfer catalysis [J].

Maruoka, K ;

Ooi, T .

CHEMICAL REVIEWS, 2003, 103 (08) :3013-3028

[38] Peptide design using α,β-dehydro amino acids:: From β-turns to helical hairpins [J].

Mathur, P ;

Ramakumar, S ;

Chauhan, VS .

BIOPOLYMERS, 2004, 76 (02) :150-161

[39] Amino Acid Schiff Base Bearing Benzophenone Imine As a Platform for Highly Congested Unnatural α-Amino Acid Synthesis [J].

Matsumoto, Yohei ;

Sawamura, Jun ;

Murata, Yumi ;

Nishikata, Takashi ;

Yazaki, Ryo ;

Ohshima, Takashi .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (18) :8498-8505

[40] SOLID PHASE PEPTIDE SYNTHESIS .1. SYNTHESIS OF A TETRAPEPTIDE [J].

MERRIFIELD, RB .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1963, 85 (14) :2149-&

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