Syntheses of Amino Acids and Amino Phosphonic Acids

氨基酸和氨基膦酸的合成

基本信息

  • 批准号:
    6533466
  • 负责人:
  • 金额:
    $ 26.34万
  • 依托单位:
  • 依托单位国家:
    美国
  • 项目类别:
  • 财政年份:
    1998
  • 资助国家:
    美国
  • 起止时间:
    1998-08-01 至 2006-07-31
  • 项目状态:
    已结题

项目摘要

DESCRIPTION (provided by applicant): Alpha-amino acids are the basic building blocks of peptides and proteins, which are responsible for the structure and function of most living things. They are extensively employed as chiral templates and subunits in the asymmetric construction of many biologically and pharmacologically active compounds. Nonproteinogenic examples are increasingly utilized to study enzyme mechanisms and to modify and enhance protein activity. Alpha-amino phosphonic acids are structural analogs of amino acids and as such exhibit a broad range of biological activities: enzyme inhibitors, antitumor agents, anti-bacterial agents, and fungicides. The principal objective of the proposed work is to develop practical and efficient methodology for the asymmetric synthesis of functionalized alpha amino acids and alpha amino phosphonic acids by exploiting the diastereoselective addition of CN and phosphite anions to chiral nonracemic sulfinimines [N-sulfinyl imines, R'S(o)N=CR2R3]. Important advantages conferred by the N-sulfinyl group include (i) powerful stereodirecting effects, (ii) activation of the C-N double bond toward addition, and (iii) facile auxiliary removal and hydrolysis of the N-sulfinyl alpha amino nitrile and alpha amino phosphonate to amino acids and amino phosphonic acids under such exceedingly mild conditions that racemization does not occur. Complementary studies will focus on the synthesis and regioselective and stereoselective ring-opening reactions of N-sulfinyl aziridine 2-phosphonates as sources of novel alpha amino phosphonic acids. The imino-Diels-Alder reactions of 2H-azirine phosphonates, a new chiral dienophile, will be exploited as sources of novel aziridine 2-phosphonates and azabicyclic systems; the latter compounds are important chiral building blocks and exhibit a range of biological activities. Such studies are expected to provide new information on the chemical reactivity/selectivity of the phosphonate group as compared to carboxylate esters. Concurrently we will employ this chemistry in syntheses of biologically relevant, functionalized alpha amino acids and alpha amino phosphonates that are difficult or impossible to prepare via other methodologies. Targets include cyclic, unsaturated, and, beta substituted derivatives (beta amino, beta hydroxy, and beta fluoro).
描述(由申请人提供):α -氨基酸是多肽和蛋白质的基本组成部分,它们负责大多数生物的结构和功能。它们被广泛用作手性模板和亚基,在许多生物和药理活性化合物的不对称结构中。非蛋白质发生的例子越来越多地用于研究酶的机制和修饰和增强蛋白质的活性。α -氨基膦酸是氨基酸的结构类似物,因此具有广泛的生物活性:酶抑制剂、抗肿瘤剂、抗菌剂和杀菌剂。

项目成果

期刊论文数量(0)
专著数量(0)
科研奖励数量(0)
会议论文数量(0)
专利数量(0)

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FRANKLIN A DAVIS其他文献

FRANKLIN A DAVIS的其他文献

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{{ truncateString('FRANKLIN A DAVIS', 18)}}的其他基金

EFFICIENT SYNTHESIS OF ENANTIOPURE ALPHA AMINO ACIDS
对映体纯α氨基酸的高效合成
  • 批准号:
    6386938
  • 财政年份:
    1998
  • 资助金额:
    $ 26.34万
  • 项目类别:
EFFICIENT SYNTHESIS OF ENANTIOPURE ALPHA AMINO ACIDS
对映体纯α氨基酸的高效合成
  • 批准号:
    6019443
  • 财政年份:
    1998
  • 资助金额:
    $ 26.34万
  • 项目类别:
Syntheses of Amino Acids and Amino Phosphonic Acids
氨基酸和氨基膦酸的合成
  • 批准号:
    6784561
  • 财政年份:
    1998
  • 资助金额:
    $ 26.34万
  • 项目类别:
Syntheses of Amino Acids and Amino Phosphonic Acids
氨基酸和氨基膦酸的合成
  • 批准号:
    6605011
  • 财政年份:
    1998
  • 资助金额:
    $ 26.34万
  • 项目类别:
EFFICIENT SYNTHESIS OF ENANTIOPURE ALPHA AMINO ACIDS
对映体纯α氨基酸的高效合成
  • 批准号:
    2670511
  • 财政年份:
    1998
  • 资助金额:
    $ 26.34万
  • 项目类别:
EFFICIENT SYNTHESIS OF ENANTIOPURE ALPHA AMINO ACIDS
对映体纯α氨基酸的高效合成
  • 批准号:
    6180957
  • 财政年份:
    1998
  • 资助金额:
    $ 26.34万
  • 项目类别:
Syntheses of Amino Acids and Amino Phosphonic Acids
氨基酸和氨基膦酸的合成
  • 批准号:
    6923593
  • 财政年份:
    1998
  • 资助金额:
    $ 26.34万
  • 项目类别:
Asymmetric Synthesis of Amino Acids and Amino Phosphonic Acids
氨基酸和氨基膦酸的不对称合成
  • 批准号:
    7477591
  • 财政年份:
    1998
  • 资助金额:
    $ 26.34万
  • 项目类别:
ASYMMETRIC SYNTHESIS OF BIOACTIVE PRIMARY AMINES
生物活性伯胺的不对称合成
  • 批准号:
    6519615
  • 财政年份:
    1995
  • 资助金额:
    $ 26.34万
  • 项目类别:
Asymmetric Synthesis of Bioactive Primary Amines
生物活性伯胺的不对称合成
  • 批准号:
    7092167
  • 财政年份:
    1995
  • 资助金额:
    $ 26.34万
  • 项目类别:
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