lyCTmnwiïïïiJCTmnTïïenffs nwitfïïi rmrr*,^ι 0
X-AAr YJ--
+ H2N—
ι ik 0
φ
*-
•AA'n—COG
Wk
X-AAr-
NH N H
^ ^ -AAV-COOR
1
X-CBZ BOC FMOC
H Alky! Amide
PeptiCLEC
PeptiCLEC-BL
TR
= Alkyl » Gly, Val. Leu
» Gly. Ala, Leu
• G l y , Val, Leu, He, Ala
• Phe. Tyr
• Phe. Tyr
• Phe, Tyr, Trp
» Arg, Lys. Met, Thr
• Pro
> Unnatural Amino Acids
• Glu, Asp. Met, Asn,
^ ^
• Glu, Asp. Met » Unnatural Amino Acids
• Val. Ala. Leu
^ff
• Phe • Unnatural Amino Acids
Arg. Lys • Unnatural Amino Acids
Here are a few examples
PeptiCLEC-TR Catalyzed Peptide Couplings
PeptiCLEC-BL Catalyzed Peptide Couplings 1. Oligopeptides
1. Oligopeptides N-Cbz-Val-PheOMe + AlaNH 2 N-Cbz-Pro-Leu-GlyOEt
PeptCLEC BL
: .
+ Phe-LeuNH 2
N-Cbz-Val-Phe-AlaNH 2
Pep,lCLECB
L
Phe-AA 2 ...AA 29 -AlaOH
N-Cbz-Pro-Leu-Gly-Phe-LeuNH 2
N-Cbz-ProOH
2. Unnatural Peptides r
^ \
r
^ W
^ \ ^
/
\ z C 0
2
M e
Phe-AA 2 ...AA 29 -Ala-PheNH 2
+ Phel\IH2
(Insulin Β chain) + Leu-GlyOEt
Pep,lCLtCTR
.
N-Cbz-Pro-Leu-GlyOEt
PepuCLEC-BL^
LeuNH 2
NHBoc
.
..
:
C0NH2
C0NH
, C02Me
ι
NHBoc
NHBoc 3. Stereospecific Synthesis of Peptidomimetics
N-Boc-Trp-Met-AspOH l\l-Boc-Ser-Lys-AlaOH N-Cbz-PheOH
ο
+ Vall\IH2 + PheNH 2
Pep CLECTR
"
~ N-Boc-Trp-Met-Asp-Val NH 2
Pep CLFCTR
"
_ N-Boc-Ser-Lys-Ala-PheNH 2
+ H-Phe-Ala-Ala-AlaOMe N-Cbz-Phe-Phe-Ala-Ala-AlaOMe
N-Cbz-Phe-CNH* N-Cbz-PheOBzl
N-Cbz-Pro-Gly-Gly-Pro-AlaOH + H-Leu-Leu-LeuNH 2
PeptiCLEC-TR
N-Cbz-Pro-Gly-Gly-Pro-Ala-Leu-Leu-Leu(\IH 2 2. Unprotected Peptides peDt,cLEc-3i_
N-Cbz-Val-PheOMe
Ο Ν"Cbz-Val-Phe- CNH.
4. Glycopeptides HOH2C N-Cbz-PheOBzl
+
H
fj0
°.
O-n-Oct
PepfCLFc-Bi,
H
+ (p-F)PheNH 2
H-Phe-Met-ArgOH
+ PheNH 2
H O ^ 1 ^ ° ,0-n-Oct
"
WLEC-TR
N-Boc-Ser-Glu-AlaOH
-
H-Trp-Met-Asp-(p-F)PheNH 2
_ H-Phe-Met-Arg-PheNH 2
+ (p-F)PheNH 2 N-Boc-Ser-Glu-Ala-(p-F)PheNH 2
OH N-Cbz-Phe(o-CI)OH
PeptiCLEC Family Products Have Unique Advantages: • Catalytic productivity: -Without recycling, produces 100 kg-5 tons/ kg catalyst -With recycling, productivity can increase 10-20 fold • Racemization-free coupling » Side chain protection usually not required ( > Simultaneous coupling and resolution
NEWFROMALTUS: PeptiKitfor Peptide Synthesis
PeptlCLEC TR
3. Unnatural Peptides
N-Cbz-Phe-OH2C
OH
H-Trp-Met-AspOH
+ PheOMe
Pep CLECTR
"
.
N-Cbz-Phe(o-CI)-PheOMe
These are just a few of the growing family of CLEG products developed and commercialized by Altus Biologies. CLEC products are pure, insoluble crystalline catalysts that conduct clean chemistry, and can be used and recycled in most reaction environments. We invite you to investigate the advantages CLEC products bring to your process by talking with an Altus applications specialist, or browsing through our web page.
A
Altus Biologies Inc. mm
40 Allston Street
t t U S
Cambridge, MA 02139-4211 USA USA Tel: 617-499-0500
Fax: 617-499-2480
Toll Free: 1-888-ALT-CLEC (258-2532) Europe Tel: +43 7673 6893 0 Internet:
[email protected] Fax: +43 7673 6893 12
Website: http://www.altus.com
PeptiCLEC and PeptiKit are trademarks of Altus Biologies Inc. © 1997 Altus Biologies Inc.. a subsidiary of Vertex Pharmaceuticals Incorporated. CIRCLE 4 ON READER SERVICE CARD
