Cyclobutane serine amino acid derivatives as 5-hydroxyproline precursors

نویسندگان

  • Benito Alcaide
  • Marta Pérez-Fernández
  • Alberto Avenoza
  • Jesús H. Busto
  • Jesús M. Peregrina
  • Fernando Rodríguez
چکیده

The synthesis of the 5-hydroxyproline derivatives 3a and 3b using cyclobutane serine analogs 1 and 2 as starting materials is reported. This process occurs with moderate cis/trans selectivity. A mechanism for this reaction is also proposed. Cyclobutane serine analog 1 was tested in tandem Michael and Wittig-like reactions, providing some evidence of the mechanism proposed.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

A Crystallization-Induced Asymmetric Transformation using Racemic Phenyl Alanine Methyl Ester Derivatives as Versatile Precursors to Prepare Amino Acids

L-Tyrosine and L-Dopa are the precursors in the biological synthesis of amine neurotransmitters. On the other hand, phenylalanine as an aromatic amino acid (AAA) is a precursor in the synthesis of L-Tyrosine and L-Dopa. For some substrates such as amino acids, resolution by the formation of diastereomers offers an attractive alternative. Among different methods in this case, crystallization-ind...

متن کامل

Impacts of gamma radiation on nutritional components of minimal processed cultured sea bass (Dicentrarchus labrax)

  Eviscerated sea bass, Dicentrarchus labrax were irradiated by Cobalt-60 at commercial irradiation facility at dose of 2.5 and 5 kGy at 2–4°C. The influences of the irradiation on proximate, fatty acid and amino acid composition in cultured sea bass were investigated. Significant differences (P < 0.0.5) were found between non-irradiated and irradiated sea bass in terms of moisture, protein, fa...

متن کامل

Chemoselective O-acylation of hydroxyamino acids and amino alcohols under acidic reaction conditions: History, scope and applications

Amino acids, whether natural, semisynthetic or synthetic, are among the most important and useful chiral building blocks available for organic chemical synthesis. In principle, they can function as inexpensive, chiral and densely functionalized starting materials. On the other hand, the use of amino acid starting materials routinely necessitates protective group chemistry, and in reality, large...

متن کامل

Microbiological Methods for the Determination of Amino Acids I. Aspartic Acid and Serine

Knowledge of the growth factor requirements of various lactic acid bacteria, especially Lactobacillus casei and L. arabinosus 17-5, has led to the development of useful microbiological methods for the quantitative determination of most-of the B vitamins. Recently attention has turned to the amino acid requirements of the lactobacilli. The amino acids necessary for growth of L. casei and L. arab...

متن کامل

Phase IIa Clinical Trial of Trans-1-Amino-3-18F-Fluoro- Cyclobutane Carboxylic Acid in Metastatic Prostate Cancer

Objective(s): We performed a phase IIa clinical trial of trans-1-amino-3-18Ffluoro-cyclobutane carboxylic acid (anti-18F-FACBC), a synthetic amino acid analog for PET, in patients with metastatic prostate cancer. Methods: The study subjects consisted of 10 untreated prostate cancer patients having lymph node and/or bone metastasis. Five patients underwent whole-body PET 5 and 30 min after intra...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:

دوره   شماره 

صفحات  -

تاریخ انتشار 2009