Fmoc-D-aspartic acid α-tert-butyl ester
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Fmoc-D-aspartic acid α-tert-butyl ester

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Category
Fmoc-Amino Acids
Catalog number
BAT-004564
CAS number
134098-70-7
Molecular Formula
C23H25NO6
Molecular Weight
411.50
Fmoc-D-aspartic acid α-tert-butyl ester
Synonyms
Fmoc-D-Asp-OtBu
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
1.251±0.06 g/cm3(Predicted)
Melting Point
103-109 ºC
Boiling Point
617.4±55.0 °C(Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C23H25NO6/c1-23(2,3)30-21(27)19(12-20(25)26)24-22(28)29-13-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,18-19H,12-13H2,1-3H3,(H,24,28)(H,25,26)/t19-/m1/s1
InChI Key
VZXQYACYLGRQJU-LJQANCHMSA-N
Canonical SMILES
CC(C)(C)OC(=O)C(CC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
1.Preparation of vitamin B6-conjugated peptides at the amino terminus and of vitamin B6-peptide-oligonucleotide conjugates.
Zhu T1, Stein S. Bioconjug Chem. 1994 Jul-Aug;5(4):312-5.
A series of N-(4'-pyridoxyl)peptides has been made by standard Fmoc chemistry and a solid-phase coupling procedure. The last Fmoc group of the peptide was removed on the synthesizer, and the free amino group was then condensed with pyridoxal. The Schiff base formed was selectively reduced using sodium cyanoborohydride. The product was cleaved from the resin using a standard procedure. No deleterious effects were found when using the protected amino acids Fmoc-L-Ala, Fmoc-L-Arg(Pmc), Fmoc-L-Asp(OtBu), Fmoc-L-His(Trt), Fmoc-L-Ser(tBu), Fmoc-L-Thr(tBu), and Fmoc-L-Cys(Trt) for peptide synthesis. A vitamin B6-peptide-oligonucleotide conjugate could be synthesized using a cysteinyl peptide and a suitably activated oligonucleotide.
2.Synthesis of various 3-substituted 1,2,4-oxadiazole-containing chiral beta 3- and alpha-amino acids from Fmoc-protected aspartic acid.
Hamzé A1, Hernandez JF, Fulcrand P, Martinez J. J Org Chem. 2003 Sep 19;68(19):7316-21.
Various 3-substituted chiral 1,2,4-oxadiazole-containing Fmoc-beta(3)- and -alpha-amino acids were synthesized from Fmoc-(l or d)-Asp(OtBu)-OH and Fmoc-l-Asp-OtBu, respectively, in three steps (i.e., condensation of an aspartyl derivative with differentially substituted amidoximes, formation of the 1,2,4-oxadiazole, and cleavage of the tert-butyl ester). These compounds represent new series of nonnatural amino acids, which could be used in combinatorial synthesis. A simple protocol has been developed to generate the 1,2,4-oxadiazole ring. Indeed, common methods resulted in cleavage of the Fmoc group or required long reaction times. We found that sodium acetate in refluxing ethanol/water (86 degrees C) was a convenient and efficient catalyst to promote conversion of Fmoc-amino acyl amidoximes to 1,2,4-oxadiazoles, and this procedure proved to be compatible with Fmoc protection. It is shown that these compounds can be prepared without significant loss of enantiomerical purity.
3.Solid-Phase Total Synthesis of Bacitracin A.
Lee J1, Griffin JH, Nicas TI. J Org Chem. 1996 Jun 14;61(12):3983-3986.
An efficient solid-phase method for the total synthesis of bacitracin A is reported. This work was undertaken in order to provide a general means of probing the intriguing mode of action of the bacitracins and exploring their potential for use against emerging drug-resistant pathogens. The synthetic approach to bacitracin A involves three key features: (1) linkage to the solid support through the side chain of the L-asparaginyl residue at position 12 (L-Asn(12)), (2) cyclization through amide bond formation between the alpha-carboxyl of L-Asn(12) and the side chain amino group of L-Lys(8), and (3) postcyclization addition of the N-terminal thiazoline dipeptide as a single unit. To initiate the synthesis, Fmoc L-Asp(OH)-OAllyl was attached to a PAL resin. The chain of bacitracin A was elaborated in the C-to-N direction by sequential piperidine deprotection/HBTU-mediated coupling cycles with Fmoc D-Asp(OtBu)-OH, Fmoc L-His(Trt)-OH, Fmoc D-Phe-OH, Fmoc L-Ile-OH, Fmoc D-Orn(Boc)-OH, Fmoc L-Lys(Aloc)-OH, Fmoc L-Ile-OH, Fmoc D-Glu(OtBu)-OH, and Fmoc L-Leu-OH.
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