An efficient synthesis of a probe for protein function: 2,3-diaminopropionic acid with orthogonal protecting groups

被引：66

作者：

Englund, EA ^{[1
]}

Gopi, HN ^{[1
]}

Appella, DH ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

来源：

ORGANIC LETTERS | 2004年 / 6卷 / 02期

关键词：

D O I：

10.1021/ol0361599

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] An efficient and cost-effective synthesis of N(alpha)-Boc(2)-N(beta)-Cbz-2,3-diaminopropionic acid is reported. The synthesis starts from commercially available N(alpha)-Boc-Asp(OBn)-OH and employs a Curtius rearrangement to establish the beta-nitrogen, Proper protection of the beta-nitrogen is essential for the success of the Curtius rearrangement.

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页码：213 / 215

页数：3

相关论文

共 15 条

[1] SYNTHESIS AND OPIOID ACTIVITY OF CONFORMATIONALLY CONSTRAINED DYNORPHIN-A ANALOGS .1. CONFORMATIONAL CONSTRAINT IN THE MESSAGE SEQUENCE [J].

ARTTAMANGKUL, S ;

MURRAY, TF ;

DELANDER, GE ;

ALDRICH, JV .

JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (13) :2410-2417

[2] alpha helix-RNA major groove recognition in an HIV-1 Rev peptide RRE RNA complex [J].

Battiste, JL ;

Mao, HY ;

Rao, NS ;

Tan, RY ;

Muhandiram, DR ;

Kay, LE ;

Frankel, AD ;

Williamson, JR .

SCIENCE, 1996, 273 (5281) :1547-1551

[3]

BODANSZKY M, 1966, PEPTIDE SYNTHESIS, pCH5

[4] CONVERSION OF ALIPHATIC AMIDES INTO AMINES WITH [I,I-BIS(TRIFLUOROACETOXY)IODO]BENZENE .2. KINETICS AND MECHANISM [J].

BOUTIN, RH ;

LOUDON, GM .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (22) :4277-4284

[5] Themes in RNA-protein recognition [J].

Draper, DE .

JOURNAL OF MOLECULAR BIOLOGY, 1999, 293 (02) :255-270

[6]

DUGGAN ME, 1989, SYNTHESIS-STUTTGART, P131

[7]

GANTE J, 1994, ANGEW CHEM INT EDIT, V33, P1699, DOI 10.1002/anie.199416991

[8] Template-nucleated alanine-lysine helices are stabilized by position-dependent interactions between the lysine side chain and the helix barrel [J].

Groebke, K ;

Renold, P ;

Tsang, KY ;

Allen, TJ ;

McClure, KF ;

Kemp, DS .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1996, 93 (09) :4025-4029

[9]

KRESTSINGER JK, 2003, J AM CHEM SOC, V125, P7907

[10] HELIX STABILIZATION BY GLU- ... LYS+ SALT BRIDGES IN SHORT PEPTIDES OF DENOVO DESIGN [J].

MARQUSEE, S ;

BALDWIN, RL .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1987, 84 (24) :8898-8902