CREBtide

CREBtide, a synthetic 13 amino acid peptide, has been reported as a PKA substrate.

Product information

CAS Number: 149155-45-3

Molecular Weight: 1716.99

Formula: C73H129N29O19

Chemical Name: (6S, 9S, 12S, 15S, 18S, 21S)-1-amino-18-sec-butyl-6-((S)-2-((S)-1-((S)-1-((S)-1-carboxy-4-guanidinobutylamino)-3-(4-hydroxyphenyl)-1-oxopropan-2-ylamino)-3-hydroxy-1-oxopropan-2-ylcarbamoyl)pyrrolidine-1-carbonyl)-21-((S)-2-((S)-2-((S)-2, 6-diaminohexanamido)-5-guanidinopentanamido)-5-guanidinopentanamido)-9-(3-guanidinopropyl)-12-(hydroxymethyl)-1-imino-15-isobutyl-8, 11, 14, 17, 20-pentaoxo-2, 7, 10, 13, 16, 19-hexaazatetracosan-24-oic acid

Smiles: [H]/N=C(\N)/NCCC[C@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCN/C(/N)=N/[H])NC(=O)[C@H](CCCN/C(/N)=N/[H])NC(=O)[C@@H](N)CCCCN)[C@@H](C)CC)C(=O)N[C@@H](CCCN/C(/N)=N/[H])C(=O)N1CCC[C@H]1C(=O)N[C@@H](CO)C(=O)N[C@@H](CC1=CC=C(O)C=C1)C(=O)N[C@@H](CCCN/C(/N)=N/[H])C(O)=O

InChiKey: QKXYCULATRFTIQ-KPXMCYQPSA-N

InChi: InChI=1S/C73H129N29O19/c1-5-39(4)55(101-60(112)46(25-26-54(106)107)94-58(110)44(16-9-29-87-70(78)79)92-57(109)43(15-8-28-86-69(76)77)91-56(108)42(75)14-6-7-27-74)66(118)98-49(34-38(2)3)61(113)99-51(36-103)63(115)93-45(17-10-30-88-71(80)81)59(111)95-47(18-11-31-89-72(82)83)67(119)102-33-13-20-53(102)65(117)100-52(37-104)64(116)97-50(35-40-21-23-41(105)24-22-40)62(114)96-48(68(120)121)19-12-32-90-73(84)85/h21-24,38-39,42-53,55,103-105H,5-20,25-37,74-75H2,1-4H3,(H,91,108)(H,92,109)(H,93,115)(H,94,110)(H,95,111)(H,96,114)(H,97,116)(H,98,118)(H,99,113)(H,100,117)(H,101,112)(H,106,107)(H,120,121)(H4,76,77,86)(H4,78,79,87)(H4,80,81,88)(H4,82,83,89)(H4,84,85,90)/t39-,42-,43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-,55-/m0/s1

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO.

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

delta-CREB is a spliced variant of cAMP response element binding protein (CREB). CREBtide (KRREILSRRPSYR), a synthetic peptide based on the phosphorylation sequence in delta-CREB. delta-CREB and CREBtide are tested as substrates of cAMP-dependent protein kinase (cAK). The apparent Km of CREBtide phosphorylation by cAK is 3.9 μM, which is 10-fold lower than that of Kemptide (Km=39 μM), the synthetic peptide substrate most often employed for cAK measurement. The Vmax values are 12.4 mumol/(min.mg) for CREBtide and 9.8 mumol/(min.mg) for Kemptide. The apparent Km of CREBtide phosphorylation by cGMP-dependent protein kinase (cGK) is 2.9 μM and the Vmax value is 3.2 mumol/(min.mg). Both delta-CREB and CREBtide are phosphorylated at a much slower rate by cGK as compared with cAK, implying that the high cAK/cGK specificity exhibits by delta-CREB is retained by the peptide.

References:

1. Wu J, et al. A microPLC-based approach for determining kinase-substrate specificity. Assay Drug Dev Technol. 2007 Aug;5(4):559-66.
2. Colbran JL, et al. cAMP-dependent protein kinase, but not the cGMP-dependent enzyme, rapidly phosphorylates delta-CREB, and a synthetic delta-CREB peptide. Biochem Cell Biol. 1992 Oct-Nov;70(10-11):1277-82.

Products are for research use only. Not for human use.