Sigma-Aldrich Fmoc-(Fmochmb)Lys(Boc)-Oh

Quality Level

200

Product Line

Novabiochem^®

Assay

≥97.0% (HPLC)
≥98% (TLC)

Form

powder

Reaction Suitability

reaction type: Fmoc solid-phase peptide synthesis

Manufacturer/Tradename

Novabiochem^®

Application(S)

peptide synthesis

Functional Group

Boc
amine

Storage Temp.

2-8°C

Inchi

1S/C49H50N2O10/c1-49(2,3)61-46(54)50-26-14-13-23-43(45(52)53)51(47(55)58-29-41-37-19-9-5-15-33(37)34-16-6-10-20-38(34)41)28-31-24-25-32(57-4)27-44(31)60-48(56)59-30-42-39-21-11-7-17-35(39)36-18-8-12-22-40(36)42/h5-12,15-22,24-25,27,41-43H,13-14,23,26,28-30H2,1-4H3,(H,50,54)(H,52,53)/t43-/m0/s1

Related Categories

Amino Acids, Resins & Reagents for Peptide Synthesis

General Description

Hmb protection of amide bonds has been shown to inhibit aggregation of "difficult" peptides by Fmoc SPPS, thereby leading to products of increased purity ^{[1,2,3,4,5,6]} . Retention of Hmb groups on the cleaved peptide can greatly improve the solubility of protected peptide fragments ^[7,8] and otherwise intractable sequences ^[9,10,11] . Furthermore, using a Hmb-protected derivative for incorporation of the residue linked to the carboxy group of Asp or Asn residues has been found to suppress formation of aspartimide and piperidide related by-products ^[12,11,14] . For a comparison of the efficiency of Hmb and pseudoprolines in preventing aggregation, see ^[15] .

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS

Literature references

T. Johnson, et Al. (1993)J. Chem. Soc., Chem. Commun., 369.
C. Hyde, et Al. (1994)Int. J. Peptide Protein Res.,43, 431.
L. C. Packman, et Al. (1994)Pept. Res.,7, 125.
T. Johnson, et Al. (1994)Tetrahedron Lett.,35, 463.
^[5] R. g. Simmonds (1996)Int. J. Peptide Protein Res.,47,36.
^[6] T. Johnson, et Al.(1995)Lett. Pept. Sci.,1, 11.
^[7] M. Quibell, et Al. (1995)J. Am. Chem. Soc.,117, 11656.
^[8] M. Quibell, et Al. (1996)J. Chem. Soc., Perkin Trans.1, 1227.
^[9] M. Quibell, et Al. (1994)Tetrahedron Lett.,35, 2237.
^[10] M. Quibell, et Al.(1994)J.Org. Chem.,59, 1745.
^[11] M. Quibell, et Al. (1995)J. Chem. Soc., Perkin Trans. 1 ,2019.
^[12] M. Quibell, et Al. (1994)J. Chem. Soc., Chem. Commun., 2343.
^[13] L. C. Packman (1995)Tetrahedron Lett.,36, 7523.
^[14] J. Offer, et Al. (1996)J. Chem. Soc., Perkin Trans.1 ,175.
^[15] W. R. Sampson, et Al. (1999)J. Peptide Sci.,5,403.

Linkage

Replaces: 04-12-1148

Analysis Note

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (TLC(157A)): ≥ 98 %
Purity (TLC(157B)): ≥ 98 %
Assay (HPLC, area%): ≥ 97.0 % (a/a)
Solubility (1 mmole in 2 mL DMF): clearly soluble

To see the solvent systems used for TLC of Novabiochem^®products please click here.Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany