• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

微生物产生的抗代谢物XVI. N5-羟基-2-甲基精氨酸和N5-羟基-2-甲基鸟氨酸的合成

Antimetabolites produced by microorganisms XVI. Synthesis of N5-hydroxy-2-methylarginine and N5-hydroxy-2-methylornithine.

作者信息

Maehr H, Leach M

出版信息

J Antibiot (Tokyo). 1978 Mar;31(3):165-9. doi: 10.7164/antibiotics.31.165.

DOI:10.7164/antibiotics.31.165
PMID:649511
Abstract

N5-Hydroxy-2-methylornithine and N5-hydroxy-2-methylarginine were synthesized. 2-Amino-5-hydroxy-2-methylpentanoic acid was prepared from 5-hydroxy-2-pentanone and converted to N-(tetrahydro-3-methyl-2-oxo-2H-pyran-3-yl) acetamide which was treated with hydrogen bromide affording 2-(acetylamino)-5-bromo-2-methylpentanoic acid. This acid was esterified with methanol and used to alkylate anti-benzaldoxime yielding methyl 2-(acetylamino)-2-methyl-5-[(phenylmethylene)amino]-pentanoate N5-oxide which, upon hydrolysis, yielded N5-hydroxy-2-methylornithine, and, upon aminolysis and short acid-treatment, gave N2-acetyl-N5-hydroxy-2-methylornithinamide. Carbamimidoylation and hydrolysis of the latter compound furnished N5-hydroxy-2-methylarginine.

摘要

合成了N5-羟基-2-甲基鸟氨酸和N5-羟基-2-甲基精氨酸。由5-羟基-2-戊酮制备2-氨基-5-羟基-2-甲基戊酸，并将其转化为N-(四氢-3-甲基-2-氧代-2H-吡喃-3-基)乙酰胺，该酰胺用溴化氢处理得到2-(乙酰氨基)-5-溴-2-甲基戊酸。该酸用甲醇酯化，用于烷基化反苯甲醛肟，得到N5-氧化物甲基2-(乙酰氨基)-2-甲基-5-[(苯基亚甲基)氨基]戊酸酯，水解后得到N5-羟基-2-甲基鸟氨酸，经氨解和短时间酸处理后得到N2-乙酰基-N5-羟基-2-甲基鸟氨酰胺。后者化合物的氨基甲脒化和水解得到N5-羟基-2-甲基精氨酸。

相似文献

1
Antimetabolites produced by microorganisms XVI. Synthesis of N5-hydroxy-2-methylarginine and N5-hydroxy-2-methylornithine.微生物产生的抗代谢物XVI. N5-羟基-2-甲基精氨酸和N5-羟基-2-甲基鸟氨酸的合成
J Antibiot (Tokyo). 1978 Mar;31(3):165-9. doi: 10.7164/antibiotics.31.165.
2
Antimetabolites produced by microorganisms. XV Synthesis of 2-methyl-L-arginine, 2-methyl-L-ornithine and their enantiomers.微生物产生的抗代谢物。XV. 2-甲基-L-精氨酸、2-甲基-L-鸟氨酸及其对映体的合成。
J Antibiot (Tokyo). 1976 Mar;29(3):221-6. doi: 10.7164/antibiotics.29.221.
3
Antimetabolites produced by microorganisms. IX. Chemical synthesis of N5-hydroxyornithine and N5-hydroxyarginine.微生物产生的抗代谢物。IX. N5-羟基鸟氨酸和N5-羟基精氨酸的化学合成。
J Org Chem. 1974 Apr 19;39(8):1166-8. doi: 10.1021/jo00922a036.
4
Synthesis and siderophore activity of albomycin-like peptides derived from N5-acetyl-N5-hydroxy-L-ornithine.源自N5-乙酰基-N5-羟基-L-鸟氨酸的白霉素样肽的合成及铁载体活性
J Med Chem. 1991 Mar;34(3):956-68. doi: 10.1021/jm00107a013.
5
Biosynthesis and stereochemical configuration of N5-(1-carboxyethyl)ornithine. An unusual amino acid produced by Streptococcus lactis.N5-(1-羧乙基)鸟氨酸的生物合成及立体化学构型。一种由乳酸链球菌产生的不寻常氨基酸。
J Biol Chem. 1987 Nov 25;262(33):16109-15.
6
Mechanistic probes of N-hydroxylation of L-arginine by the inducible nitric oxide synthase from murine macrophages.
Biochemistry. 1992 Jul 28;31(29):6822-8. doi: 10.1021/bi00144a024.
7
Synthetic approaches to N(delta)-methylated L-arginine, N(omega)-hydroxy-L-arginine, L-citrulline, and N(delta)-cyano-L-ornithine.
J Org Chem. 2008 Feb 1;73(3):1025-30. doi: 10.1021/jo702150d. Epub 2008 Jan 8.
8
Synthesis of 2-methyl and 2-carboxymethyl derivatives of ornithine and arginine.鸟氨酸和精氨酸的2-甲基及2-羧甲基衍生物的合成。
Int J Pept Protein Res. 1983 Jul;22(1):50-6. doi: 10.1111/j.1399-3011.1983.tb02067.x.
9
[Metabolites of microorganisms. 130. Synthesis of delta-N-hydroxy-L-arginine].[微生物代谢产物。130. δ-N-羟基-L-精氨酸的合成]
Helv Chim Acta. 1974 Apr 27;57(3):657-64. doi: 10.1002/hlca.19740570318.
10
Antimetabolites produced by microorganisms. 8. N5-hydroxy-L-arginine, a new naturally occurring amino acid.微生物产生的抗代谢物。8. N5-羟基-L-精氨酸，一种新的天然存在的氨基酸。
J Antibiot (Tokyo). 1973 May;26(5):284-8.