L-Alanine-2,3,3,3-d4-N-FMOC - CAS 225101-69-9
Molecular Formula:
CD3CD(NH-FMOC)COOH
Molecular Weight:
315.36
COA:
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Tag:
Fmoc-protected Amino Acids (Labelled)
Description:
L-Alanine-2,3,3,3-d4-N-FMOC is a labelled L-Alanine-N-FMOC. Alanine is one of the non-essential amino acids for humans. Alanine is the key compound in glucose-alanine cycle.
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Purity:
95% by HPLC; 98% atom D
Related CAS:
35661-39-3 (unlabelled)
Synonyms:
FMOC-L-Alanine-d4; FMOC-L-Ala-OH-d4; (2S)-2,3,3,3-tetradeuterio-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acid
MSDS:
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InChIKey:
QWXZOFZKSQXPDC-UAMNTACQSA-N
InChI:
InChI=1S/C18H17NO4/c1-11(17(20)21)19-18(22)23-10-16-14-8-4-2-6-12(14)13-7-3-5-9-15(13)16/h2-9,11,16H,10H2,1H3,(H,19,22)(H,20,21)/t11-/m0/s1/i1D3,11D
Canonical SMILES:
CC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
1.Substrate recognition mechanism of carboxypeptidase Y.
Nakase H1, Murata S, Ueno H, Hayashi R. Biosci Biotechnol Biochem. 2001 Nov;65(11):2465-71.
To clarify the substrate-recognition mechanism of carboxypeptidase Y, Fmoc-(Glu)n Ala-OH (n = 1 to 6), Fmoc-(Glu)n Ala-NH2 (1 to 5), and Fmoc-Lys(Glu)3Ala-NH2 were synthesized, and kinetic parameters for these substrates were measured. Km for Fmoc-peptides significantly decreased as peptide length increased from n = 1 to n = 5 with only slight changes in kcat. Km for Fmoc-(Glu)(5,6)Ala-OH were almost the same as one for protein substrates described previously (Nakase et al., Bull. Chem. Soc. Jpn., 73, 2587-2590). These results show that the enzyme has six subsites (S1' and S1-S5). Each subsite affinity calculated from the Km revealed subsite properties, and from the differences of subsite affinity between pH 6.5 and 5.0, the residues in each subsite were predicted. For Fmoc-peptide amide substrates, the priorities of amidase and carboxamide peptidase activities were dependent on the substrate. It is likely that the interactions between side chains of peptide and subsites compensate for the lack of P1'-S1' interaction, so the amidase activity prevailed for Fmoc-(Glu)(3,5)Ala-NH2.
2.Fmoc-2-mercaptobenzothiazole, for the introduction of the Fmoc moiety free of side-reactions.
Isidro-Llobet A1, Just-Baringo X, Ewenson A, Alvarez M, Albericio F. Biopolymers. 2007;88(5):733-7.
A double side-reaction, consisting in the formation of Fmoc-beta-Ala-OH and Fmoc-beta-Ala-AA-OH, during the preparation of Fmoc protected amino acids (Fmoc-AA-OH) with Fmoc-OSu is discussed. Furthermore, the new Fmoc-2-MBT reagent is proposed for avoiding these side-reactions as well as the formation of the Fmoc-dipeptides (Fmoc-AA-AA-OH) and even tripeptides, which is another important side-reaction when chloroformates such as Fmoc-Cl is used for the protection of the alpha-amino function of the amino acids.
3.Friendly strategy to prepare encoded one bead-one compound cyclic peptide library.
Giudicessi SL1, Gurevich-Messina JM, Martínez-Ceron MC, Erra-Balsells R, Albericio F, Cascone O, Camperi SA. ACS Comb Sci. 2013 Oct 14;15(10):525-9. doi: 10.1021/co400039a. Epub 2013 Sep 6.
One bead-one peptide libraries allow the screening of suitable ligands for any target protein. Short cyclic peptides are ideal ligands for affinity chromatography because of their high affinity and selectivity for the target protein and stability against proteases. We designed a library synthesis strategy to facilitate the identification of cyclic peptides by MS consisting of (a) sequential incorporation of a mixture of Fmoc-Ala-OH and Fmoc-Asp[2-phenylisopropyl (OPp)]-OH (15:85) to Gly-oxymethylbenzamide-ChemMatrix (Gly-HMBA-CM) resin, (b) synthesis of the combinatorial library on the resin by the divide-couple-recombine method, (c) removal of OPp with 4% TFA, (d) peptide cyclization on solid phase through side-chain Asp and amino terminus, and (e) removal of side chain protecting groups with a 95% TFA cocktail. Peptides were cleaved from the beads with ammonia and the linear code was sequenced by MALDI-TOF MS/MS. The high capacity of ChemMatrix resin together with the sensitivity of MS allows code sequencing from a single bead.
4.Relative toxicities and neuromuscular nicotinic receptor agonistic potencies of anabasine enantiomers and anabaseine.
Lee ST1, Wildeboer K, Panter KE, Kem WR, Gardner DR, Molyneux RJ, Chang CW, Soti F, Pfister JA. Neurotoxicol Teratol. 2006 Mar-Apr;28(2):220-8. Epub 2006 Feb 20.
Anabasine occurring in wild tree tobacco (Nicotiana glauca) and anabaseine occurring in certain animal venoms are nicotinic receptor agonist toxins. Anabasine lacks the imine double bond of anabaseine; the two possible enantiomers of anabasine occur in N. glauca. A comparision of the relative potencies of S- and R-anabasine has not been previously reported. We separated the enantiomers of anabasine by reaction of the racemic N. glauca natural product with 9-fluorenylmethoxycarbonyl-L-alanine (Fmoc-L-Ala-OH) to give diastereomers, which were separated by preparative reversed phase HPLC. The S- and R-anabasine enantiomer fractions were then obtained by Edman degradation. A mouse bioassay was used to determine the relative lethalities of S- and R-enriched anabasine enantiomers. The intravenous LD50 of the (+)-R-anabasine rich fraction was 11 +/- 1.0 mg/kg and that of the (-)-S-anabasine-rich fraction was 16 +/- 1.0 mg/kg. The LD50 of anabaseine was 0.
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Chemical Structure

CAS 225101-69-9 L-Alanine-2,3,3,3-d4-N-FMOC

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