Didehydroamino Acids (DDAA) and Didehydropeptides (DDP)

Schmidt, Ulrich; Lieberknecht, Albrecht; Wild, Jochen

doi:10.1055/s-1988-27503

Cited by 240 publications

(124 citation statements)

References 0 publications

Supporting

Mentioning

123

Contrasting

Order By: Relevance

“…Chiral a,b-didehydroamino acid (DDAA) derivatives 43 are important building blocks for the synthesis of acyclic amino acids by hydrogenation reactions. 44,2f Moreover, they are especially suitable compounds for cyclopropanation and cycloaddition reactions affording 1-aminocyclopropane-1-carboxylic acids (ACCs) 2l,45 and cyclic and bicyclic a-amino acids.…”

Section: Chiral Ab-didehydroamino Acid Derivativesmentioning

confidence: 99%

From α-Amino Acids to Peptides: All You Need for the Journey

Nájera¹

2002

Synlett

View full text Add to dashboard Cite

Abstract:In this account several tools necessary for the synthesis of peptides from a-amino acids are considered. Different strategies for the asymmetric synthesis of a-amino acids are studied. New chiral glycine and alanine imines as acyclic and cyclic templates for the asymmetric synthesis of different types of mono as well as dialkylated a-amino acids with acyclic and heterocyclic structures are reviewed. Their diastereoselective alkylation and final hydrolysis takes place under very mild reaction conditions. New polymer-supported cinchonidine and cinchonine ammonium salts and chiral binaphthol-derived aminoalkoxides (BINOLAMs), have been developed as catalysts for the asymmetric PTC alkylation of imino esters. The use of chiral oxazinone and pyrazinone a,b-didehydroamino acid derivatives in hydrogenation, Heck-arylation, cyclopropanation and Diels-Alder cycloaddition reactions for the asymmetric synthesis of a-amino acids are also studied. Azomethine ylides derived from saturated oxazinones can also be used in the asymmetric synthesis of prolines by means of diastereoselective dipolar cycloadditions. For the protection of a-amino acids new efficient reagents, Fmoc-P-OSu and Cbz-P-OSu, derived from poly(styrene-co-N-hydroxymaleimide) named as polymeric N-hydroxysuccinimide (P-HOSu), have been developed. Several new systems such as polymer-supported P-HOSu/DCC and polystyrenebound P-TBTU or P-HBTU, together with non-polymeric thiouronium salts derived from 2-mercaptopyridine-1-oxide and TMU, such as HOTT and TOTT, and from DMPU, such as HODT and TODT, have been used as peptide coupling reagents, in solution and solid phase peptide synthesis, as well as for the preparation of primary amides, Weinreb amides and other hydroxamates, directly from carboxylic acids.

show abstract

Section: Chiral Ab-didehydroamino Acid Derivativesmentioning

confidence: 99%

From α-Amino Acids to Peptides: All You Need for the Journey

Nájera¹

2002

Synlett

View full text Add to dashboard Cite

show abstract

“…[71][72]76 The synthesis of α,β-dehydro-α-amino acids, including their synthesis from α-(dialkoxyphosphoryl)glycinates in the Wadsworth-Emmons reaction, was the subject matter of a few excellent reviews. 60,[71][72][73] The most frequently used and very useful procedure for preparing a wide variety of α,β-dehydro-α-amino acids from N-acyl-α-(dialkoxyphosphoryl)glycinates 3b was developed by Schmidt et. al.…”

Section: Scheme 25mentioning

confidence: 99%

α-Amino acid derivatives with a Cα-P bond in organic synthesis

Mazurkiewicz¹,

Kuźnik²,

Grymel³

et al. 2007

Arkivoc

View full text Add to dashboard Cite

α-Amino acid derivatives with a C α -P bond have been used for a wide range of chemical transformations, including synthesis of many kinds of bioactive compounds, e.g. nonproteinogenic α-amino acids, α,β-dehydro-α-amino acids, dehydropeptides, β-lactam antibiotics and glycopeptides. The present review is focused on methods of synthesis of the title compounds, their properties and application in organic synthesis.

show abstract

“…[16,17] The antibacterial activity of β-lactams and also of glycopeptide antibiotics (such as, for instance, vancomycin) -the most widely used compounds -is due to inhibition of key steps in cell wall biosynthesis. [ myl peptides 17, 37, 40, 42, 44, 46, and 49a and 49b, which, after deprotection, afforded the desired target molecules muramyl-L-alanine (38), muramyl-L-alanyl-D-glutamic acid (39), muramyl-L-alanyl-D-glutaminide (41), muramyl-L-alanyl-Disoglutaminyl-L-lysine (43), muramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (45), muramyl-L-alanyl-L-isoglutaminyl-(2S,6R)-2,6-diaminopimelinyl-D-alanine (47) (AA) n ϭ n amino acids, with n ϭ 0Ϫ5 ever, the emergence of bacterial resistance to these antibiotics is a good reason to investigate the effects of partial structures of peptidoglycans further. [18,19] Bacterial infections result in an immune response that starts with the production of proinflammatory mediators such as cytokines TNF-α and interleukins-1 and -6.…”

Section: Introductionmentioning

confidence: 99%