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Chirality, Amino Acid Racemization, and the Authenticity of the Buyid Silks

By Suzanne R. Carpenter

Chirality, Amino Acid Racemization, and the Authenticity of the Buyid Silks


 

Abstract

This case study is designed to walk biochemistry majors through the science behind a journal article about an investigation of potential fraud hinging on the analysis of a non-natural enantiomer of aspartic acid (“Buyid Silk and the Tale of Bibi Shahrbanu,” Analytical Chemistry 89, 2017). The case focuses on the famous Buyid silk forgery, where textiles once believed to be from the Persian Buyid period (934–1062 BCE) were later suspected to be modern forgeries. In Part I, students review the basics of chiral centers, laying the foundation for understanding enantiomerism in biological molecules. In Part II, they explore the technique of aspartic acid racemization, a method used to date artifacts and, in this case, assess the authenticity of the silks. Part I is appropriate for students who have completed a general chemistry sequence or the first semester of a general, organic, and biological (GOB) chemistry sequence. Part II would be appropriate for students who are currently enrolled in or who have completed the second semester of an organic chemistry sequence, as it covers carboxylic acid derivatives and their reactivity.

   

Date Posted

10/07/2024

Overview

Objectives

  • Identify chiral centers in organic molecules and determine their absolute configurations.
  • Represent chiral centers using Fischer projections.
  • Describe the process of racemization for chiral centers alpha to a carbonyl group.
  • Explain why aspartic acid has the fastest racemization rate of the naturally occurring amino acids.

Keywords

Chiral centers; absolute configuration; racemization; Fischer projections; aspartic acid; Buyid silk; enantiomerism; forgery

  

Subject Headings

Biochemistry
Chemistry (General)
Organic Chemistry

EDUCATIONAL LEVEL

Undergraduate lower division, Undergraduate upper division

  

FORMAT

PDF

   

TOPICAL AREAS

N/A

   

LANGUAGE

English

   

TYPE/METHODS

Journal Article

 

 

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