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Racemization in peptide synthesis

Y. AsanoSyntheses of useful amides and amino acids by the use of new microbial enzymes (in Japanese), 65, 710-712 (1991).

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Peptide racemization mechanism. Kinetic isotope effect …

Y. Asano, K. Kishino, A. Yamada, S. Hanamoto and K. Kondo
Plasmid-based, D-aminopeptidase-catalysed synthesis of ()-amino acids. 110, 206-208 (1991).

Solid Phase Peptide Synthesis; Aggregation, Racemization and Side Reactions; ..

For the coupling of very bulky amino acids such as N-alkylamino acids or α-dialkylamino acids, the moderately reactive TBTU should be replaced by more potent reagents such as HATU [16], TATU, or PyBOP [25].

Mechanism of the racemization of amino acids

Y. AsanoSyntheses of useful amides and amino acids by the use of new microbial enzymes (in Japanese),  65, 1617-1626 (1991).

Generally speaking, the first priority is to reach the optimal combination of high coupling rate and minimal racemization. Indeed contrary to widespread assumptions Nα-urethane protected amino acids can racemize considerably under inadequate coupling conditions [12,13,14].

Racemization can occur following cyclization of the activated species to a 5(4H)-oxa-zolone which racemizes via enolization and the subsequent reopening by the amino component yields epimers.

Aggregation, Racemization and Side Reactions - Peptide

and Liu, Y.-M.: Sequential Analysis of D/L-Amino Acid in Peptide with a Novel Chiral Edman Degradation Method.

In peptide synthesis diketopiperazine formation is a notorious side-reaction at the dipeptide stage and is particularly prone to occur in Fmoc based SPPS because of its mechanism.

The same is true for the activation of Fmoc-His(Trt)-OH since racemization catalyzed by the nitrogen of the imidazole ring may occur. For the coupling of especially bulky amino acids such as Aib, Tic, ... or in the case of recognized difficult coupling we recommend the replacement of HOBt by HOAt, or the use of other activating agents.

16/01/2018 · CHEMICAL COMMUNICATIONS, 1967 691 Racemization in Peptide Synthesis
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  • Kinetics of racemization of arylglycines



    Aggreation, racemization and side reactions all lead to peptide impurities and reduced yields

  • Overview of Solid Phase Peptide Synthesis (SPPS)

    Kinetics of racemization of ..

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Reductive Amination of Aldehydes and Ketones ..

Organic chemistry: “Introduction to amino acids and peptides”. Biochemistry. How to draw amino acids. Acid/base properties of amino acids. Finding net charge of amino acids and peptides (proteins) at a specified pH. of amino acids and peptides. Peptide (amide) bonds. Amino acid sequencing with partial digestion by enzymes such as . Total acid hydrolysis (TAH)

RECENT PUBLICATIONS - Toyama Prefectural University

Organic chemistry: “Amino acids and peptides”. Biochemistry--amino acids, peptides, and polypeptide sequencing. Acid/base properties of amino acids. How to draw amino acids at various . How to determine of a peptide; . of the N-terminus; conversion of the C-terminus into an amide. Total acid hydrolysis (TAH). Sanger’s reagent and chloride. Hydrazine (NH2NH2). enzymes--, , . A polypeptide sequencing problem

10.1056/NEJMoa072761 - New England Journal of Medicine

Organic chemistry: “Amino acid and polypeptide synthesis”. Amino acid synthesis--Gabriel synthesis; synthesis. degradation. Polypeptide synthesis-- () and () amino-protecting groups; protection of the terminus via ester formation; DCC () -activating reagent. An example of calculating and charge at a specific pH for a long polypeptide

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