Amino Acids:
Chromatographic Separation
and Enantioresolution

Ravi Bhushan and Juergen Martens

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March 2010
322 pp.
(hardcover)

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Illustrated:
ISBN: 978-0-9728061-3-8

 

缯span> Contents

1. Amino Acids and Separation Techniques

I. Introduction

A. Amino Acids

B. Preparation of Test Materials

II. Separation Techniques

A. Thin-Layer Chromatography (TLC)

B. Impregnated TLC

C. High-Performance Liquid Chromatography (HPLC)

D. Separation and Chromatography

E. Approach to Separation of Enantiomers

References

 

2. Marfeyⳍ Reagent for Indirect Resolution of Enantiomers

I. Introduction

II. Derivatization Reactions

A. MarfeyⳠReagent

References

 

 

3. Indirect TLC Enantiomeric Separation of Proteinogenic
Amino Acids: Application of FDAA and FDNP-l-Phe-NH2,
and FDNP-l-Val-NH2, FDNP-l-Leu-NH2

I. Application of MR

A. Enantiomeric Resolution via FDAA Diastereomers

B. Separation of FDAA Derivatives by 2D TLC

II. Application of Chiral Variants of MR

A. TLC of Proteinogenic Amino Acids

B. Mobile Phase in TLC

C. Further Advantages of MR

D. Chiral Variants and Derivatization

III. Separation of Diastereomers Prepared With FDNP-
l-Ala-NH2, FDNP-l-Phe-NH2, and FDNP-l-Val-NH2

A. NP TLC

B. RP TLC

IV. Separation of Diastereomers Prepared With
FDNP-l-Leu-NH2

A. NP-TLC

B. RP-TLC

References

 

4. Indirect TLC and HPLC Enantiomeric Separation of
Nonprotein Amino Acids: Application of CDRs Containing
l-Ala-NH2, l-Phe-NH2, l-Val-NH2, l-Leu-NH2, l-Pro-NH2,
l-Met-NH2, and d-Phg-NH2 as the Chiral Auxiliaries in
FDNP Moiety

I. Introduction to Nonprotein Amino Acids

II. Synthesis of CDRs and Their Chiral Purity

A. Synthesis of CDRs Having Amino Acid Amides as the
Chiral Auxiliary

B. Synthesis of CDRs Having Amino Acid as the
Chiral Auxiliary

III. Derivatization of Nonprotein dl-a-Amino Acids

IV. TLC Separation of Diastereomers Prepared With
FDNP-l-Ala-NH2, FDNP-l-Phe-NH2, FDNP-l-Val-NH2,
FDNP-l-Leu-NH2, and FDNP-l-Pro-NH2

A. NP-TLC

B. RP-TLC

C. RP- vs NP-TLC

V. Separation by HPLC

A. Separation of Diastereomers Prepared With
FDNP-l-Ala-NH2, FDNP-l-Phe-NH2, FDNP-l-Val-NH2,
and FDNP-l-Pro-NH2 Using C8 Column

B. Separation of Diastereomers Prepared With
FDNP-l-Ala-NH2, FDNP-l-Met-NH2, FDNP-d-Phg-NH2,
and FDNP-l-Leu-NH2 Using C18 Column

VI. HPLC Using CDRs Having Amino Acids as the Chiral
Moiety (FDNP-l-Ala, FDNP-l-Val, FDNP-l-Phe,
FDNP-l-Leu)

A. The CDRs and the Diastereomers

B. HPLC Analysis of Multicomponent Mixture and
Simultaneous Enantioresolution

VI. Separation Mechanism

References

 

5. Indirect TLC Enantiomeric Separation of Proteinogenic
Amino Acids: Application of FDAA and FDNP-l-Phe-NH2,
and FDNP-l-Val-NH2, FDNP-l-Leu-NH2

I. FDAA (MR)

II. Chiral Variants of MR

III. Application of FDNP-l-Met-NH2, FDNP-d-Phg-NH2,

and FDNP-l-Leu-NH2

A. Derivatization

B. Chromatographic conditions

C. Separation of Diastereomers Prepared With FDNP-l-Met-NH2

D. Separation of Diastereomers Prepared With
FDNP-d-Phg-NH2

E. FDNP-l-Leu-NH2

IV. Separation Efficiency and Performance of

FDNP-l-Met-NH2 and FDNP-d-Phg-NH2

V. Effect of amino acid side-chain

VI. HPLC Using CDRs Having Amino Acids as the Chiral

Moiety (FDNP-l-Ala, FDNP-l-Val,

FDNP-l-Phe, FDNP-l-Leu)

A. The CDRs and the Diastereomers

B. HPLC Separation of Diastereomers

VII. Other CDRs

A. (S)-NIFE: (S)-N-(4-Nitrophenoxycarbonyl)

Phenylalanine Methoxyethyl Ester

B. DANI: (1S,2S)- or (1R,2R)-1,3-Diacetoxy 1-(4-nitro-

phenyl)-2-propylisothiocyanate; [(S,S)- or (R,R)-DANI]

C. (+)-FLEC: (+)-1-( 9-Fluorenyl)ethyl Chloroformate

References

 

6. Indirect HPLC Enantiomeric Separation of Proteinogenic
Amino Acids: Application of CDRs Based on Cyanuric
Chloride: Structural Analogy of the Diastereomers With
MR

I. Cyanuric Chloride in Chiral Chromatography

II. Trifuctionality of Cyanuric Chloride

III. CC Based CDRs Analogous to MR

A. Synthesis of Chiral DCT Reagents

B. Synthesis of Chiral MCT Reagents

C. Synthesis of Diastereomers of Amino acids

IV. HPLC

A. Separation of Diastereomers Prepared With DCTs

B. Separation of Diastereomers Prepared With MCTs

V. Separation Mechanism

References

 

7. Enantioresolution of dl-Penicillamine

I. dl-Penicillamine

II. TLC Resolution

A. Direct resolution Using l-Tartaric Acid and
(R)-Mandelic Acid as Chiral Impregnating Reagent
or Chiral Mobile Phase Additive (CMPA)

B. Indirect Resolution Using MR and Its Variants

A. Indirect Resolution Using MR and Its Variants as the CDRs

B. Indirect Resolution Using SuccinimidyL-(S)-Naproxen
Ester as the CDR

C. Resolution by Using Tagging

References

 

8. Direct TLC Separation of Enantiomers of dl-Amino Acids
and Their Derivatives

I. Introduction

II. Resolution of dl-Amino Acids

A. Ligand Exchange

B. Mixing the Chiral Selector With Silica Gel Slurry

III. Resolution of Enantiomers of Dansyl Amino Acids

A. Impregnation With Amino Acids as Chiral Selectors

B. Impregnation With b-CD

C. Impregnation With Macrocyclic Antibiotics

IV. Resolution of Enantiomers of PTH Amino Acid

V. Mechanism of Separation

A. Ion Exchange

B. Ligand Exchange

VI. Direct TLC Resolution on Cellulose Plates

VII. Amino Acids as Chiral Selectors

References

 

9. TLC Separation of Amino Acids and Their Derivatives

I. Introduction

II. Separation by Impregnation of Thin Layers

A. Amino Acids

B. Derivatives of Amino Acids

III. Separation on Plain Plates

A. Amino Acids

B. Derivatives of Amino Acids

IV. Quantification

A. Amino Acids

B. PTH Amino Acids

C. DNP Amino Acids

References

 

Appendix: Bibliographic Survey of the Analytes, Column, Mobile
Phase, and CDR for Indirect Enantioseparation of Amino Acids

Abbreviations and Acronyms

Index

About the Authors | Preface

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