8.52068

Fmoc-(FmocHmb)Lys(Boc)-OH

Novabiochem^®

• 동의어(들): Fmoc-(FmocHmb)Lys(Boc)-OH, N-α-Fmoc-N-α-(2-Fmoc-oxy-4-methoxybenzyl)-N-ε-t.-butoxycarbonyl-L-lysine
• 실험식(Hill 표기법): C₄₉H₅₀N₂O₁₀
• CAS Number: 166881-56-7
• Molecular Weight: 826.93
• MDL number: MFCD00797868
• UNSPSC 코드: 12352209
• NACRES: NA.22

속성

• Quality Level: 200
• 제품 라인: Novabiochem^®
• 분석: ≥97.0% (HPLC); ≥98% (TLC)
• 양식: powder
• 반응 적합성: reaction type: Fmoc solid-phase peptide synthesis
• 제조업체/상표: Novabiochem^®
• 응용 분야: peptide synthesis
• 작용기: Boc; amine
• 저장 온도: 2-8°C
• SMILES string: N([C@@H](CCCCNC(=O)OC(C)(C)C)C(=O)O)(Cc4c(cc(cc4)OC)OC(=O)OCC5c6c(cccc6)c7c5cccc7)C(=O)OCC1c2c(cccc2)c3c1cccc3
• 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
• InChI key: XQEJYVQFPXBQOZ-QLKFWGTOSA-N

설명

일반 설명

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

^[1] T. Johnson, et al. (1993) J. Chem. Soc., Chem. Commun., 369.
^[2] C. Hyde, et al. (1994) Int. J. Peptide Protein Res., 43, 431.
^[3] L. C. Packman, et al. (1994) Pept. Res., 7, 125.
^[4] 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.

결합

Replaces: 04-12-1148

분석 메모

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.

법적 정보

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

안전성 정보

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable