90048-49-0

Upstream product

• 56-45-1 L-serin 
• 71432-55-8 2-tert-butyl-1,3-diisopropylisourea 
• 59859-77-7 2-benzyloxycarbonylamino-3-hydroxy-propionic acid tert-butyl ester 
• 202868-77-7 O-(phenylmethyl)-L-serine 1,1-dimethylethyl ester 
• 540-88-5 acetic acid tert-butyl ester 
• 71630-31-4 N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester 
• 118867-04-2 Z-Ser(Bz)-O^tBu 
• 59859-77-7 2-benzyloxycarbonylamino-3-hydroxy-propionic Acid tert-butyl Ester 

Downstream Products

• 312933-67-8 N-(2,3,4,6-Tetra-O-acetyl-D-galactopyranosyloxycarbonyl)-L-phenylalanyl-L-serine tert-butyl ester 
• 389806-01-3 N-(2-nitrobenzenesulfonyl)-L-serine tert-butyl ester 
• 937393-46-9 Nα-2,3-dibenzyloxybenzoyl-Nδ-benzyloxycarbonyl-L-ornithinyl-L-serine tert-butyl ester 
• 937393-48-1 Nα-2,3-dibenzyloxybenzoyl-Nδ-benzyloxycarbonyl-D-ornithinyl-L-serine tert-butyl ester 
• 1224637-32-4 N,N-dibezyl-L-serine tert-butyl ester 
• 71630-31-4 N-(tert-butyloxycarbonyl)-L-serine tert-butyl ester 
• 110797-35-8 N-[(9-fluorenyl)methoxycarbonyl]-L-serine tert-butyl ester 
• 107082-54-2 N-(tert-butyloxycarbonyl)-α,β-dehydroalanine tert-butyl ester 
• 108492-14-4 tert-butyl (S)-3-azido-2-((tert-butoxycarbonyl)amino)propanoate 
• 132903-68-5 N-benzylserine tert-butyl ester 
• 1415318-24-9 N-benzyl-2-(4-hydroxybenzamido)tert-butylacrylate 
• 127700-57-6 1-p-toluensulfonylaziridine-(2S)-carboxylic acid tert-butyl ester 
• 116400-16-9 N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine 1,1-dimethylethyl ester 
• 151436-20-3 tert-butyl (S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoate 

Relevant academic research and scientific papers

Optimized syntheses of Fmoc azido amino acids for the preparation of azidopeptides

The rise of CuI-catalyzed click chemistry has initiated an increased demand for azido and alkyne derivatives of amino acid as precursors for the synthesis of clicked peptides. However, the use of azido and alkyne amino acids in peptide chemistry is complicated by their high cost. For this reason, we investigated the possibility of the in-house preparation of a set of five Fmoc azido amino acids: β-azido l-alanine and d-alanine, γ-azido l-homoalanine, δ-azido l-ornithine and ω-azido l-lysine. We investigated several reaction pathways described in the literature, suggested several improvements and proposed several alternative routes for the synthesis of these compounds in high purity. Here, we demonstrate that multigram quantities of these Fmoc azido amino acids can be prepared within a week or two and at user-friendly costs. We also incorporated these azido amino acids into several model tripeptides, and we observed the formation of a new elimination product of the azido moiety upon conditions of prolonged couplings with 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate/DIPEA. We hope that our detailed synthetic protocols will inspire some peptide chemists to prepare these Fmoc azido acids in their laboratories and will assist them in avoiding the too extensive costs of azidopeptide syntheses. Experimental procedures and/or analytical data for compounds 3–5, 20, 25, 26, 30 and 43–47 are provided in the supporting information.

Improved enantioselective synthesis of protected (3S,4S)-4-amino-3,5- dihydroxypentanoic acid (ADPA)

An improved enantioselective synthesis of protected (3S,4S)-4-amino-3,5- dihydroxypentanoic acid (ADPA) from L-serine has been developed. Enantioselectivity is improved by replacing the methyl ester with the tert-butyl ester and using neutral magnesium salt of esters to give β-keto ester.

Vanchrobactin: absolute configuration and total synthesis

The stereochemistry of vanchrobactin, a siderophore produced by the bacterial fish pathogenVibrio anguillarum serotype O2, was elucidated by chiral capillary electrophoresis analysis and total synthesis as N-[N′-(2,3-dihydroxybenzoyl)-d-arginyl]-l-serine.

Towards new MraY inhibitors: A serine template for uracil and 5-amino-5-deoxyribosyl scaffolding

The bacterial translocase MraY is a good target for the development of new antitbiotics as it is ubiquitous and essential for bacterial growth. The goal of this work was the synthesis of simplified analogues of naturally occurring inhibitors of this enzyme to investigate the essential character of the uridine moiety of these inhibitors with regards to biological activity. Thus, the structure of the targeted enantiomerically pure N-(uracilylpentyl)-β-D-O- (5-amino-5-deoxyribosyl)-L-serine retains uracil and 5-amino-5-deoxyribose parts linked by a serinyl template. The synthetic strategy towards this compound relies on sequential O-glycosylation and N-alkylation by reductive amination of a serine derivative. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

CIDOFOVIR PEPTIDE CONJUGATES AS PRODRUGS

Cidofovir-based compounds having an amino acid, dipeptide or tripeptide attached to a cidofovir or cyclic cidofovir framework. The compounds show enhanced oral bioavailability and increased binding to the PepT1 transporter. The present invention also provides compositions and methods for treating virus infections, and a method of preparing cidofovir.

2, 3, 4, 5-TETRAHYDRO-1H-[1, 4] BENZODIAZEPINE-3-HYDROXAMIC ACIDS AS MATRIX METALLOPROTEINASE INHIBITORS

Compounds having formula (1) are useful in treating disease conditions mediated by matrix metalloproteinases and TACE, such as tumor growth, osteoarthritis, rheumatoid arthritis and degenerative cartilage loss.

Synthesis of β-lactams via ring opening of a serine derived aziridine

Serine derived aziridine 15 was successfully ring-opened with amino acid esters to give diaminopropionic acid derivatives in excellent yield and regioselectivity. These compounds were cyclised to form the corresponding β-lactams in good overall yield. One

Use of (S)-N-tert-butoxycarbonylaziridine-2-carboxylate derivatives for α-amino acid synthesis

(S)-tert-Butyl-N-tert-butoxycarbonylaziridine-2-carboxylate and (S)-tert-butyl-N-tert-butoxycarbonylaziridine-2-carboxamide were synthesised and found to react with copper 'catalysed' Grignard reagents to give protected α-amino acids in moderate to good yields.

Efficient synthesis of tosyl-aziridine-2-t-butyl carboxylate

Tosyl-aziridine-2-t-butyl carboxylate is easily synthesized from Tos-Ser-O-(t)Bu by use of Mitsunobu conditions.