2008
DOI: 10.1055/s-0028-1087490
|View full text |Cite
|
Sign up to set email alerts
|

Enantioselective Preparation of β²-Amino Acid Derivatives for β-Peptide Synthesis

Abstract: Enantioselective Preparation of b 2 -Amino Acid Derivatives for b-Peptide Synthesis b 2 -A m i n o A c i d D e r i v a t i v e s f o r b -P e p t i d e S y n t h e s i sAbstract: b-Amino acids with a single side chain in the a-position (b 2 -amino acids or H-b 2 hXaa(PG)-OH; i.e., homo-amino acids with proteinogenic side chains) have turned out to be important components in b-peptides. They contribute to unique secondary structures, they are required for mimicking the structure and the activity of bturn-formin… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1

Citation Types

0
63
0

Year Published

2010
2010
2021
2021

Publication Types

Select...
5
3

Relationship

1
7

Authors

Journals

citations
Cited by 145 publications
(63 citation statements)
references
References 61 publications
0
63
0
Order By: Relevance
“…As is depicted in Figure 5, the former amino acid serves as a building block for peptides with anti-thrombotic 28 and anti-arthritic 29 potential. The L-β 3 -phenylalanine building block, in turn, is useful for the assembly of β-peptides, 30 whereas the D-β-hydroxy ester obtained directly from the CaADH reduction serves is a precursor for the important anti-depressent, fluoxetine. 31 Finally, the D-γ-hydroxy ester itself is a valuable chiron for the assembly of crytophycin, 32 and L-γ 4 -homophenylalanine is as useful monomer for γ-peptides.…”
mentioning
confidence: 99%
“…As is depicted in Figure 5, the former amino acid serves as a building block for peptides with anti-thrombotic 28 and anti-arthritic 29 potential. The L-β 3 -phenylalanine building block, in turn, is useful for the assembly of β-peptides, 30 whereas the D-β-hydroxy ester obtained directly from the CaADH reduction serves is a precursor for the important anti-depressent, fluoxetine. 31 Finally, the D-γ-hydroxy ester itself is a valuable chiron for the assembly of crytophycin, 32 and L-γ 4 -homophenylalanine is as useful monomer for γ-peptides.…”
mentioning
confidence: 99%
“…Most of these methods are chemical in nature [319][320][321], but enzymatic methods applying, for instance, a lipase [322,323], aminoacylase [324], penicillin G acylase [325], peptide deformylase [9], and aminomutase [326] have also been described (for a review see Reference [327]). An enzyme with activity toward a b-amino acid amide was described in 2005 by Komeda and Asano [82].…”
Section: Synthesis Of Enantiopure B-amino Acids By B-aminopeptidasesmentioning
confidence: 99%
“…[12] Hence, alternative enzymatic approaches to the enantioselective production of b 2 -amino acids are highly desirable to complement chemical asymmetric-synthesis strategies. The highly S enantioselective reactions of BapA with a model b 2 -dipeptide indicate that baminopeptidases could become useful for the biocatalytic production of enantiopure b 2 -amino acids by the kinetic resolution of racemic b 2 -amino acid derivatives, for example, b 2 -amino acid amides or esters.…”
mentioning
confidence: 99%
“…Classical chemical-resolution strategies to obtain enantiopure b 2 -amino acids from racemic starting materials have so far been unsuccessful. [12] The b-aminopeptidases BapA from Sphingosinicella xenopeptidilytica and DmpA from Ochrobactrum anthropi recently aroused interest because they can catalyze the degradation of b 3 -peptides with proteinogenic side chains that are otherwise stable to proteolytic breakdown. [2,13] Despite sharing an amino acid sequence identity of 42 %, BapA and DmpA differ with respect to their substrate specificities.…”
mentioning
confidence: 99%