Merck
CN
All Photos(1)

Documents

Safety Information

8.52068

Sigma-Aldrich

Fmoc-(FmocHmb)Lys(Boc)-OH

Novabiochem®

Sign Into View Organizational & Contract Pricing

Synonym(s):
Fmoc-(FmocHmb)Lys(Boc)-OH, N-α-Fmoc-N-α-(2-Fmoc-oxy-4-methoxybenzyl)-N-ε-t.-butoxycarbonyl-L-lysine
Empirical Formula (Hill Notation):
C49H50N2O10
CAS Number:
Molecular Weight:
826.93

Quality Level

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

InChI key

XQEJYVQFPXBQOZ-QLKFWGTOSA-N

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

[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.

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.

Legal Information

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

新产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Documents related to the products that you have purchased in the past have been gathered in the Document Library for your convenience.

Visit the Document Library

Difficulty Finding Your Product Or Lot/Batch Number?

Product numbers are combined with Pack Sizes/Quantity when displayed on the website (example: T1503-25G). Please make sure you enter ONLY the product number in the Product Number field (example: T1503).

Example:

T1503
Product Number
-
25G
Pack Size/Quantity

Additional examples:

705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

Having trouble? Feel free to contact Technical Service for assistance.

Lot and Batch Numbers can be found on a product's label following the words 'Lot' or 'Batch'.

Aldrich Products

  • For a lot number such as TO09019TO, enter it as 09019TO (without the first two letters 'TO').

  • For a lot number with a filling-code such as 05427ES-021, enter it as 05427ES (without the filling-code '-021').

  • For a lot number with a filling-code such as STBB0728K9, enter it as STBB0728 without the filling-code 'K9'.

Not Finding What You Are Looking For?

In some cases, a COA may not be available online. If your search was unable to find the COA you can request one.

Request COA

Protocols

The ease of assembly of a given peptide sequence is hard to predict, which makes peptide synthesis challenging. Review methods and reagents for avoiding aggregation in solid-phase peptide synthesis.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service