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13254-07-4

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Formation and isolation of simple, stable, acyclic di- and tripeptide hemiacetals
Di- and tripeptide aldehydes were found to undergo reaction with methanol to afford the corresponding methyl hemiacetals. These compounds, which possessed unusual stability, were isolated and characterized using NMR techniques and a chemical correlation experiment.
Miller, John F.,Spaltenstein, Andrew
p. 2521 - 2524
(1996)
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Microwave irradiated high-speed solution synthesis of peptide acids employing Fmoc-amino acid pentafluorophenyl esters as coupling agents
A high-speed solution phase synthesis of peptide acids employing commercially available Fmoc-amino acid pentafluorophenyl esters as coupling agents has been demonstrated. The coupling has been found to be fast and completed in 30-45 sec. A simple work-up of the reaction mixture has resulted N-protected peptide acids in good yield. Utilizing the present method, the coupling of difficult sequences containing highly hindered α, α-dialkyl amino acids has also been demonstrated. Further, the synthesis of diastereomeric dipeptides, Fmoc-Phg-Phe-OMe and Fmoc-D-Phg-Phe-OMe revealed that the coupling is free from racemization.
Suresh Babu, Vommina V.,Ramana Rao
p. 2328 - 2332
(2007/10/03)

Peptide synthesis in aqueous solution. IV. Preparation and properties of [p-(benzyloxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate, [p-(t-butoxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate and [p-(9-fluorenylmethyl-oxycarbonyloxy)phenyl]dimethylsulfonium methyl sulfate as water-soluble N-acylating reagents
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Azuse,Tamura,Kinomura,Okai,Kouge,Hamatsu,Koizumi
p. 3103 - 3108
(2007/10/02)

Glycopeptide Synthesis: Selective C-terminal Deblocking and Peptide Chain Elongation of Glucosylserine Derivatives
Benzyloxycarbonyl-(Z-)serine 2-bromoethyl ester (3b) reacts with 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl bromide (14) to give the glucosylserine ester 15.After conversion into the corresponding 2-iodoethyl ester 23 the carboxylic group is deblocked selectively by reductive elimination using zinc.In this procedure the Z and the carbohydrate protective functions as well as the sensitive O-glycoside bond remain unaffected.The glycosylserine 24 is condensed with amino acid 2-bromoethyl esters 2 to form protected glycodipeptide 2-bromoethyl esters 18 which are extended to give glycotripeptide esters 25 after selective carboxyl deblocking.Whereas protected serine dipeptides 5 are glycosylated with 14 to form the conjugates 18, the glycosylation of the serine tripeptides 10 was not successful.
Buchholz, Michael,Kunz, Horst
p. 1859 - 1885
(2007/10/02)

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Chemical Properties

Melting Point: 166-167 °C
Boiling Point: 654.9 °C at 760 mmHg
Flash Point:349.9 °C
Density: 1.193 g/cm³
Storage Temp.:-15°C
Vapor Pressure: 4.78E-18mmHg at 25°C
Refractive Index: 1.564
PKA: 3.54±0.10(Predicted)
PSA: 104.73000
LogP: 3.92140

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