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Amino Acids: |
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Ravi Bhushan and Juergen Martens |
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$99.75 |
March 2010 |
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Illustrated: |
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· 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. Marfey’s
Reagent for Indirect Resolution of Enantiomers
I. Introduction
II. Derivatization Reactions
A. Marfey’s Reagent
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